Formaldehyde → HCID 66733152, compound

HRID 1519466Notes

Reaction equation

HRID 1519466 reaction equation
[ClH:1].Cl.[Cl:3][C:4]1[CH:43]=[CH:42][C:7]2[NH:8][CH2:9][CH2:10][CH2:11][CH:12]([O:13][C:14]([CH:16]([N:36]3[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]3)[C:17](=[O:35])[C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:33])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[CH3:32])=[CH:20][C:19]=3[CH3:34])=[O:15])[C:6]=2[CH:5]=1.C=O.[C:46]([O-])(=O)C.[Na+].[B-]C#N.[Na+].[OH-].[Na+]>O.CO>[ClH:3].[ClH:1].[Cl:3][C:4]1[CH:43]=[CH:42][C:7]2[NH:8][CH2:9][CH2:10][CH2:11][CH:12]([O:13][C:14]([CH:16]([N:36]3[CH2:37][CH2:38][N:39]([CH3:46])[CH2:40][CH2:41]3)[C:17](=[O:35])[C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:33])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[CH3:32])=[CH:20][C:19]=3[CH3:34])=[O:15])[C:6]=2[CH:5]=1

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 20587905Sodium cyanoborohydride [MI]HCID 66732904HCID 66732904, compound

Product 1

HCID 66733152HCID 66733152, compoundYield 116.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1-{7-Chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yloxycarbonylmethyl}-piperazine dihydrochloride (400 mg, 0.62 mmol), formalin (0.15 ml, 1.9 mmol), sodium acetate (61 mg, 0.74 mmol), and sodium cyanotrihydroborate (119 mg, 1.9 mmol) were added to methanol (5 ml), and the mixture was stirred at room temperature for 1 hour. Water and aqueous sodium hydroxide solution were added to the reaction mixture, and the precipitates were collected by filtration, washed with water, and then dried. The obtained solid was dissolved in ethyl acetate, and a 4N hydrogen chloride ethyl acetate solution (0.5 ml) was added thereto. The precipitates were then collected by filtration, washed with ethyl acetate and dried to obtain 240 mg of 1-{7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yloxycarbonylmethyl}-4-methyl-piperazine dihydrochloride as white powder.

Workup

  1. filtrationthe precipitates were collected by filtration
  2. washwashed with water
  3. customdried
  4. dissolutionThe obtained solid was dissolved in ethyl acetate
  5. additiona 4N hydrogen chloride ethyl acetate solution (0.5 ml) was added
  6. filtrationThe precipitates were then collected by filtration
  7. washwashed with ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-71e8b631d1364483ab7c9013574a2b18
Source dataset
uspto-grants-2015_07
Patent number
US09073868B2

Reaction notes

Loading…