Formaldehyde → HCID 66830708, compound

HRID 1686909Notes

Reaction equation

HRID 1686909 reaction equation
[Cl:1][C:2]1[C:3]([NH:20][C:21]2[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=2[C:23]([NH:25][CH3:26])=[O:24])=[N:4][C:5]([NH:8][C:9]2[CH:19]=[CH:18][C:12]3[CH2:13][CH2:14][NH:15][CH2:16][CH2:17][C:11]=3[CH:10]=2)=[N:6][CH:7]=1.C=O.[C:33]([BH3-])#N.[Na+]>C(#N)C>[Cl:1][C:2]1[C:3]([NH:20][C:21]2[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=2[C:23]([NH:25][CH3:26])=[O:24])=[N:4][C:5]([NH:8][C:9]2[CH:19]=[CH:18][C:12]3[CH2:13][CH2:14][N:15]([CH3:33])[CH2:16][CH2:17][C:11]=3[CH:10]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 25156760HCID 25156760, compound

Product 1

HCID 66830708HCID 66830708, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-[5-Chloro-2-(2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamide was suspended in acetonitrile (5 mL). Aqueous formaldehyde (37%, 325 μL/4 mmol) and sodium cyanoborohydride (210 mg/3.3 mmol) were added sequentially and the reaction stirred at room temperature for two hours. The material was concentrated onto celite and the desired product was isolated by sequential column chromatography on silica gel (eluting with 0→50% methanol/methylene chloride) followed by basic alumina (eluting with 0→40% methanol/methylene chloride). Yield 50 mg/35%. 1H NMR (400 MHz, DMSO-d6) δ 11.58 (s, 1H), 9.41 (s, 1H), 8.82-8.69 (m, 2H), 8.22 (s, 1H), 7.79 (d, J=7.8 Hz, 1H), 7.56-7.41 (m, 3H), 7.19 (dd, J=7.3, 7.3 Hz, 1H), 7.09 (d, J=8.1 Hz, 1H), 3.19-2.78 (m, 14H). LC/MS found 436 (M+H). mp 125-130° C. (dec.).

Workup

  1. concentrationThe material was concentrated onto celite

Sources & evidence

ORD record
ord-a4187c12f51147cf9c0538c5d3733137
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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