Acetic Acid → HCID 178480934, compound

HRID 51620Notes

Reaction equation

HRID 51620 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16]([NH2:18])=[N:15][CH:14]=[N:13][C:12]=3[N:11]([C@H:19]3[CH2:24][CH2:23][C@@H:22]([N:25]4[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]4)[CH2:21][CH2:20]3)[CH:10]=2)=[CH:5][CH:4]=1.[CH:32](=O)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[BH4-].[Na+]>ClCCCl>[CH2:32]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[C:16]([NH2:18])=[N:15][CH:14]=[N:13][C:12]=3[N:11]([C@H:19]3[CH2:24][CH2:23][C@@H:22]([N:25]4[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH2:30]4)[CH2:21][CH2:20]3)[CH:10]=2)=[CH:7][CH:8]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 4311764Sodium borohydrideHCID 5049666Sodium triacetoxyborohydrideHCID 178480932HCID 178480932, compound

Product 1

HCID 178480934HCID 178480934, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of cis-5-[4-(aminomethyl)phenyl]-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (100 mg, 0.238 mmol), benzaldehyde (28 mg, 0.262 mmol) and acetic acid (43 mg, 0.714 mmol) in 1,2 dichloroethane (4 mL) was stirred at ambient temperature for 1 hour. Sodium triacetoxyborohydride (100 mg, 2.6 mmol) was added and the mixture was stirring continued for 2 hours. Sodium borohydride (100 mg, 2.60 mmol) was added and stirring was continued for an additional 30 minutes, the solvents were removed under reduced pressure and the residue purified by preparative reverse phase chromatography to yield cis-5-{4-[(benzylamino)methyl]phenyl}-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine: 1H NMR (DMSO-d6, 400 MHz) δ 8.13(s, 1H), 7.2-7.50(m, 1OH), 6.03(bs, 2H), 4.67 (m, 1H), 3.71(d, 2H), 1.52-2.50(m, 20H); R-P-HPLC (Hypersil HS C18, 5 μm, 100 A, 250×4.6 mm; 5%-50% acetonitrile over 25 min, 1 mL/min) tr 14.42 min.; MS:MH+ 510.3.

Workup

  1. stirringthe mixture was stirring
  2. waitcontinued for 2 hours
  3. stirringstirring
  4. waitwas continued for an additional 30 minutes
  5. customthe solvents were removed under reduced pressure
  6. customthe residue purified by preparative reverse phase chromatography

Sources & evidence

ORD record
ord-60e10ec8a84d47bc806ab37a3ce15dfa
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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