Acetyl chloride → HCID 67202714, compound

HRID 1505979Notes

Reaction equation

HRID 1505979 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:19]3[C:20]4[CH:26]=[C:25]([C:27]5[CH:28]=[N:29][N:30]([CH3:32])[CH:31]=5)[CH:24]=[N:23][C:21]=4[NH:22][C:18]=3[CH:17]=[N:16][C:15]=2[C:33]#[N:34])[CH2:9]1)=O)(C)(C)C.C([Cl:38])(=O)C>CO>[ClH:38].[CH3:32][N:30]1[CH:31]=[C:27]([C:25]2[CH:24]=[N:23][C:21]3[NH:22][C:18]4[CH:17]=[N:16][C:15]([C:33]#[N:34])=[C:14]([O:13][CH:10]5[CH2:11][CH2:12][NH:8][CH2:9]5)[C:19]=4[C:20]=3[CH:26]=2)[CH:28]=[N:29]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 58266784HCID 58266784, compound

Product 1

HCID 67202714HCID 67202714, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[6-Cyano-3-(1-methyl-1H-pyrazol-4-yl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-5-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl ester (28 mg, 0.06 mmol) was treated with a mixture of acetyl chloride and methanol (2:5, 1 mL). After 1 h the mixture was concentrated in vacuo and the resultant residue was triturated with acetonitrile, the solid collected by filtration and dried in vacuo to afford the compound as a yellow solid (25 mg, 100%). 1H NMR (DMSO-D6, 400 MHz): 13.07 (s, 1H), 9.83 (s, 1H), 9.63 (s, 1H), 8.99 (d, J=2.1 Hz, 1H), 8.82 (s, 1H), 8.58 (d, J=2.1 Hz, 1H), 8.45 (s, 1H), 8.11 (d, J=0.8 Hz, 1H), 5.68-5.61 (m, 1H), 3.98-3.88 (m, 5H), 3.62-3.43 (m, 2H), 2.43-2.34 (m, 1H), 2.29-2.17 (m, 1H). LCMS (Method A): RT=4.97 min, M+H+=360.

Workup

  1. concentrationAfter 1 h the mixture was concentrated in vacuo
  2. customthe resultant residue was triturated with acetonitrile
  3. filtrationthe solid collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-354d78d5c9b145b383d1492ad59f921d
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

Loading…