Benzylamine → HCID 57559138, compound

HRID 736109Notes

Reaction equation

HRID 736109 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([N:8]2[CH2:21][CH2:20][C:19]3[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[NH:12][C:11]=3[CH:10]([C:22]([OH:24])=O)[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:39]([NH2:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl>[CH2:39]([NH:46][C:22]([C:10]1[C:11]2[NH:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:19]=2[CH2:20][CH2:21][N:8]([C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:26][CH:25]=2)[CH:9]=1)=[O:24])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 66641242HCID 66641242, compound

Product 1

HCID 57559138HCID 57559138, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of 3-(4-fluorobenzoyl)-1,2,3,4,5,6-hexahydro-azepino[4,5-b]indole-5-carboxylic acid (176 mg, 0.5 mmol) in DCM (3 mL) was added carbonyldiimidazole (97 mg, 0.6 mol) and the mixture was stirred for 1 hour at 20° C. Benzylamine (109 μL, 1 mmol) was added and the mixture was stirred overnight. Solid was collected by filtration and washed by DCM and dried under high vacuum to give the title compound (90 mg); 93% MS (ES): 442 (MH+).

Workup

  1. stirringthe mixture was stirred overnight
  2. filtrationSolid was collected by filtration
  3. washwashed by DCM
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-4d1eba3a4aa447778510921c12c9e161
Source dataset
uspto-grants-2009_09
Patent number
US07595311B2

Reaction notes

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