Propanal → HCID 136128373, compound

HRID 220947Notes

Reaction equation

HRID 220947 reaction equation
[CH:1](=O)[CH2:2][CH3:3].Cl.[Cl:6][C:7]1[CH:22]=[C:21]([C:23]([N:25]2[CH2:34][C:33]3[CH:32]=[N:31][N:30]([CH3:35])[C:29]=3[NH:28][C:27]3[CH:36]=[CH:37][CH:38]=[CH:39][C:26]2=3)=[O:24])[CH:20]=[CH:19][C:8]=1[CH2:9][NH:10][C:11]([CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:12].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CCN(C(C)C)C(C)C.CN(C=O)C>[Cl:6][C:7]1[CH:22]=[C:21]([C:23]([N:25]2[CH2:34][C:33]3[CH:32]=[N:31][N:30]([CH3:35])[C:29]=3[NH:28][C:27]3[CH:36]=[CH:37][CH:38]=[CH:39][C:26]2=3)=[O:24])[CH:20]=[CH:19][C:8]=1[CH2:9][NH:10][C:11]([CH:13]1[CH2:14][CH2:15][N:16]([CH2:1][CH2:2][CH3:3])[CH2:17][CH2:18]1)=[O:12]

Participants

7

Reactant 3

HCID 527PropanalHCID 5049666Sodium triacetoxyborohydrideHCID 136346645HCID 136346645, compound

Product 1

HCID 136128373HCID 136128373, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolvent2×HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A solution of propionaldehyde (0.29 mg, 0.005 mmol) in 1,2-dichloroethane (0.05 ml) was added to a solution of piperidine-4-carboxylic acid 2-chloro-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-benzylamide hydrochloride (Compound number 1109) (2.8 mg, 0.005 mmol) in 1,2-dichloroethane (0.05 ml) and DIEA (0.0026 ml). The mixture was stirred at room temperature for 1 h then a solution of sodium triacetoxyborohydride (1.59 mg, 0.0075 mmol) in DMF (0.05 ml) was added. The mixture was stirred for 20 h at room temperature then solvents were removed in vacuo to yield the title compound. (ESI)+: [M+H]+=521.4

Workup

  1. stirringThe mixture was stirred for 20 h at room temperature
  2. customsolvents were removed in vacuo

Sources & evidence

ORD record
ord-a11e3b5c8c134fcdb6689ef3bd312aed
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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