Hydrochloric Acid → HCID 46929280, compound

HRID 1801492Notes

Reaction equation

HRID 1801492 reaction equation
[N:1]1[C:6]2[C:7]3[CH:19]=[CH:18][CH:17]=[N:16][C:8]=3[NH:9][C:10]3[CH:15]=[N:14][CH:13]=[CH:12][C:11]=3[C:5]=2[CH:4]=[N:3][C:2]=1[NH:20][CH:21]1[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]1.Cl>O1CCOCC1>[NH:24]1[CH2:23][CH2:22][CH:21]([NH:20][C:2]2[N:3]=[CH:4][C:5]3[C:11]4[CH:12]=[CH:13][N:14]=[CH:15][C:10]=4[NH:9][C:8]4[N:16]=[CH:17][CH:18]=[CH:19][C:7]=4[C:6]=3[N:1]=2)[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59506325HCID 59506325, compound

Product 1

HCID 46929280HCID 46929280, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The compound, N-(piperidin-4-yl)-9H-dipyrido[2,3-b:4′,3′-f]pyrimido[4,5-d]azepin-2-amine was synthesized using three step procedure shown above. The first two steps provided the intermediate, tert-butyl 4-((9H-dipyrido[2,3-b:4′,3′-f]pyrimido[4,5-d]azepin-2-yl)amino)piperidine-1-carboxylate, which was prepared using 6,11-dihydro-5H-dipyrido[2,3-b:4′,3′-f]azepin-5-one and 1-(1-(tert-butoxycarbonyl)piperidin-4-yl)guanidinium chloride as described in the General procedure A. The desired compound, N-(piperidin-4-yl)-9H-dipyrido[2,3-b:4′,3′-f]pyrimido[4,5-d]azepin-2-amine was obtained by treating tert-butyl 4-((9H-dipyrido[2,3-b:4′,3′-f]pyrimido[4,5-d]azepin-2-yl)amino)piperidine-1-carboxylate with a solution of HCl (gas) in 1,4-Dioxane (3 mL) for 4 hour. The solvent was then removed under reduced pressure and the crude product was purified using reverse phase chromatography to give the desired product as yellow solid and a TFA salt (0.025 g, 40%); M.p.=189-191° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.71 (bs, 2H), 8.58 (s, 1H), 8.48 (s, 1H), 8.38 (s, 1H), 8.29-8.26 (m, 2H), 7.88 (bs, 1H), 7.52-7.51 (d, J=5.4 Hz, 1H), 7.13-7.10 (m, 1H), 4.19 (bs, 2H), 3.40-3.39 (bd, 1H), 3.21-3.18 (bd, 1H), 2.86-2.53 (m, 2H), 1.98-1.57 (m, 4H); LCMS (M+H)=346.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe crude product was purified

Sources & evidence

ORD record
ord-e1be560014ee43d5bcf3166828e18522
Source dataset
uspto-grants-2013_01
Patent number
US08349827B2

Reaction notes

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