Phosgene → HCID 57731554, compound

HRID 2234716Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[O:23][CH3:24])=[CH:15][N:14]([S:25]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=4)(=[O:27])=[O:26])[C:11]3=[N:12][CH:13]=2)=[CH:4][C:3]=1[C:35]([N:37]1[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]1)=[O:36].C(NC(C)C)(C)C.[C:51](Cl)(Cl)=[O:52].[NH:55]1[CH2:60][CH2:59][O:58][CH2:57][CH2:56]1>ClCCl>[CH3:24][O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:16]1[C:10]2[C:11](=[N:12][CH:13]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:51]([N:55]4[CH2:60][CH2:59][O:58][CH2:57][CH2:56]4)=[O:52])=[C:3]([C:35]([N:37]4[CH2:38][CH2:39][N:40]([CH3:43])[CH2:41][CH2:42]4)=[O:36])[CH:4]=3)[CH:9]=2)[N:14]([S:25]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)(=[O:27])=[O:26])[CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Crude {2-amino-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-(4-methyl-piperazin-1-yl)-methanone (0.637 mmol) was dissolved in dichloromethane (7.0 mL) with di-iso-propylamine (266 μL, 1.91 mmol) and cooled to 0° C. Phosgene (20% w/v in toluene, 1.0 mL, 1.91 mmol) was added and after 1 minute, morpholine (557 μL, 6.37 mmol) was added rapidly. The mixture was stirred 15 h, washed with brine and dried over sodium sulfate to afford crude morpholine-4-carboxylic acid [4-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-(4-methyl-piperazine-1-carbonyl)-phenyl]-amide (632 mg, crude). MS: m/z 710 (M+H+).

Workup

washwashed with brine
dry with materialdried over sodium sulfate

Sources & evidence

ORD record: ord-a5b9e9daf9b3463590fd0cd18b43e2ff
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709645B2

Reaction notes

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