1-Chloroethyl chloroformate → HCID 44546425, compound

HRID 1505996Notes

Reaction equation

HRID 1505996 reaction equation
C1(S([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:37]#[N:38])=[C:18]([O:19][CH:20]4[CH2:23][N:22](C(C5C=CC=CC=5)C5C=CC=CC=5)[CH2:21]4)[C:13]=3[C:12]3[CH:39]=[C:40]([C:43]4[CH:44]=[N:45][N:46]([CH3:48])[CH:47]=4)[CH:41]=[N:42][C:11]2=3)(=O)=O)C=CC=CC=1.ClC(OC(Cl)C)=O>CO.C(Cl)Cl>[NH:22]1[CH2:21][CH:20]([O:19][C:18]2[C:13]3[C:12]4[CH:39]=[C:40]([C:43]5[CH:44]=[N:45][N:46]([CH3:48])[CH:47]=5)[CH:41]=[N:42][C:11]=4[NH:10][C:14]=3[CH:15]=[N:16][C:17]=2[C:37]#[N:38])[CH2:23]1

Participants

5

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 67027536HCID 67027536, compound

Product 1

HCID 44546425HCID 44546425, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 9-benzenesulfonyl-5-(1-benzhydrylazetidin-3-yloxy)-3-(1-methyl-1H-pyrazol-4-yl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (238 mg, 0.37 mmol) in methanol (10 mL) at 0° C. was added a solution of 1-chloroethyl chloroformate (120 μL, 1.1 mmol) in DCM (10 mL). The reaction mixture was allowed to warm to ambient temperature then heated at 40° C. for 4 h. The reaction was cooled to ambient temperature and then concentrated in vacuo. Purification of the residue by flash chromatography (silica, 11 g column, SPE NH2, 0-20% methanol in DCM) afforded the title compound as a white solid (5 mg, 5%). 1H NMR (CDCl3 plus CD3OD, 400 MHz): 8.85 (s, 1H), 8.74-8.69 (m, 2H), 8.08 (s, 1H), 7.93 (s, 1H), 5.73-5.64 (m, 1H), 4.19-4.05 (m, 4H), 4.01 (s, 3H). LCMS (Method G): RT=5.59 min, M+H+=346.

Workup

  1. temperaturethen heated at 40° C. for 4 h
  2. temperatureThe reaction was cooled to ambient temperature
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by flash chromatography (silica, 11 g column, SPE NH2, 0-20% methanol in DCM)

Sources & evidence

ORD record
ord-0b1c714ae47f4b10ad01cb269cc820aa
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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