N-Methylbutylamine → HCID 21913048, compound

HRID 1352641Notes

Reaction equation

HRID 1352641 reaction equation
CC1N2N=NN=C2C2N=C(CCC)N(CCCS(C3C=CC(C(Cl)=O)=CC=3)(=O)=O)C=2C=1C.CNCCCC.N1CCOCC1.[CH2:45]([N:49]([CH3:81])[C:50](=[O:80])[C:51]1[CH:56]=[CH:55][C:54]([S:57]([CH2:60][CH2:61][CH2:62][N:63]2[C:71]3[C:70]([CH3:72])=[C:69]([CH3:73])[N:68]4N=N[N:76]=[C:67]4[C:66]=3[N:65]=[C:64]2[CH2:77][CH2:78][CH3:79])(=[O:59])=[O:58])=[CH:53][CH:52]=1)[CH2:46][CH2:47][CH3:48]>ClCCl>[NH2:76][C:67]1[C:66]2[N:65]=[C:64]([CH2:77][CH2:78][CH3:79])[N:63]([CH2:62][CH2:61][CH2:60][S:57]([C:54]3[CH:55]=[CH:56][C:51]([C:50]([N:49]([CH2:45][CH2:46][CH2:47][CH3:48])[CH3:81])=[O:80])=[CH:52][CH:53]=3)(=[O:59])=[O:58])[C:71]=2[C:70]([CH3:72])=[C:69]([CH3:73])[N:68]=1

Participants

6

Reactant 4

HCID 8068N-Methylbutylamine2×HCID 8083MorpholineHCID 21913131HCID 21913131, compoundHCID 21913486HCID 21913486, compound

Product 1

HCID 21913048HCID 21913048, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The general methods described in Example 101 were used with the following modifications. To one-third of the crude solution of 4-[3-(5,6-dimethyl-8-propyl-7H-imidazo[4,5-c]tetrazolo[1,5-a]pyridin-7-yl)propane-1-sulfonyl]benzoyl chloride in dichloromethane, described in Part B of Example 101, was added N-methyl butylamine (0.583 mL, 4.92 mmol) in lieu of morpholine, and the reaction was stirred overnight. Additional N-methyl butylamine (0.5 mL) was added, and the reaction was stirred for two hours. The crude product was recrystallized from ethyl acetate:hexane, and the crystals were dried for three hours in a vacuum oven at 90° C. N-Butyl-4-[3-(5,6-dimethyl-8-propyl-7H-imidazo[4,5-c]tetrazolo[1,5-a]pyridin-7-yl)propane-1-sulfonyl]N-methyl benzamide (770 mg, 1.46 mmol) was treated as described in Part C of Example 101. The crude product was recrystallized from ethyl acetate:hexane with a couple drops of methanol to provide crystals, which were isolated by filtration, washed with hexane, and dried for four hours under high vacuum at 50° C. to provide 0.56 g of 4-[3-(4-amino-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-1-yl)propane-1-sulfonyl]-N-butyl-N-methylbenzamide as a white powder, mp 127.0–129.0° C. 1H NMR (300 MHz, CDCl3) δ 7.95 (d, J=8.4, 2H), 7.58 (d, J=8.4, 2H), 4.92 (br s, 2H), 4.42 (dd, J=7.8, 7.8, 2H), 3.55 (dd, J=7.8, 7.8, 1H), 3.21–3.05 (m, 4.5 H), 2.90 (s, 1.5 H), 2.77 (dd, J=7.7, 7.7, 2H), 2.43 (s, 3H), 2.39 (s, 3H), 2.23 (quint, J=7.6, 2H), 1.93–1.36 (m, 5H), 1.15 (quart, J=7.5, 1H), 1.07 (t, J=7.4, 3H), 0.99 (t, J=7.0, 1.5H), 0.81 (t, J=7.4, 1.5H);

Workup

  1. stirringthe reaction was stirred for two hours
  2. customThe crude product was recrystallized from ethyl acetate
  3. dry with materialhexane, and the crystals were dried for three hours in a vacuum oven at 90° C
  4. customThe crude product was recrystallized from ethyl acetate
  5. customhexane with a couple drops of methanol to provide crystals
  6. customwhich were isolated by filtration
  7. washwashed with hexane
  8. customdried for four hours under high vacuum at 50° C.

Sources & evidence

ORD record
ord-5df9eeb25e1f4d6f9cd44e3c93567193
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

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