Hydrochloric Acid → HCID 10227348, compound

HRID 346759Notes

Reaction equation

HRID 346759 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:24][CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)=[CH:14][C:13]=2[NH:32][S:33]([CH3:36])(=[O:35])=[O:34])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[ClH:37].CCOCC>CO.C(OCC)(=O)C>[ClH:37].[N:18]1([C:15]2[CH:16]=[CH:17][C:12]([NH:11][S:8]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)(=[O:9])=[O:10])=[C:13]([NH:32][S:33]([CH3:36])(=[O:34])=[O:35])[CH:14]=2)[CH2:24][CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 22272552HCID 22272552, compound

Product 1

HCID 10227348HCID 10227348, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 4-{4-{[(4-methylphenyl)sulfonyl]amino}-3-[(methylsulfonyl)amino]phenyl}-1,4-diazepane-1-carboxylate (0.5 g) was dissolved in methanol (15 mL). A solution of HCl in ethyl acetate (1N, 25 mL) was added and the mixture stirred for 2 hours. Ether (200 mL) was added and the mixture stirred for 3 hours to allow full precipitation. The product was collected by filtration, washed with ether and dried. Yield 0.43 g (98%) 1H NMR (400 MHz, DMSO-d6) δ 2.03 (m, 2 H), 2.36 (s, 3 H), 2.9 (s, 3H), 3.02–3.09 (br m, 2 H), 3.11–3.19 (br m, 2 H), 3.41 (br t, J=7.08 Hz, 2 H), 3.63 (br m, 2 H), 6.46 (d ab, J=2.8 Hz, 8.8 Hz, 1 H), 6.62 (ab, J=8.8 Hz, 1 H), 6.71 (d, J=2.8 Hz, 1 H), 7.36 (ab, J=8.3 Hz, 2 H), 7.58 (ab, J=8.3 Hz, 2 H), 8.39 (s, 1 H), 9.2 (br, 2 H). 9.8 (s, 1 H), MS (ESI+) for C19H27N4O4S2 m/z 439.148 (M+H)+ (Calculated 439.1474).

Workup

  1. stirringthe mixture stirred for 3 hours
  2. customprecipitation
  3. filtrationThe product was collected by filtration
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-1915eee3c34649f29be70a1fd730322d
Source dataset
uspto-grants-2007_02
Patent number
US07173035B2

Reaction notes

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