Dichloromethane → HCID 131736918, compound

HRID 56383Notes

Reaction equation

[NH2:1][C@@H:2]1[C@H:6]([NH:7][C:8]2[N:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:18]4[C:23]([Cl:24])=[C:22]([O:25][CH3:26])[CH:21]=[C:20]([O:27][CH3:28])[C:19]=4[Cl:29])[CH:14]=3)[N:9]=2)[CH2:5][N:4]([C:30]([O-:32])=[O:31])[CH2:3]1.CCN([CH:39]([CH3:41])[CH3:40])C(C)C.[C:42](Cl)(=[O:45])[CH:43]=[CH2:44].Cl[CH2:48]Cl>>[C:42]([NH:1][C@@H:2]1[C@H:6]([NH:7][C:8]2[N:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:18]4[C:19]([Cl:29])=[C:20]([O:27][CH3:28])[CH:21]=[C:22]([O:25][CH3:26])[C:23]=4[Cl:24])[CH:14]=3)[N:9]=2)[CH2:5][N:4]([C:30]([O:32][C:39]([CH3:40])([CH3:41])[CH3:48])=[O:31])[CH2:3]1)(=[O:45])[CH:43]=[CH2:44]

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 13140Acryloyl chloride

HCID 81531Diisopropylethylamine

HCID 131736919HCID 131736919, compound

Product 1

HCID 131736918HCID 131736918, compoundYield 52%

Procedure

To a solution of (3S,4R)-3-amino-4-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)pyrrolidine-1-carboxylate (2.1 g, 4.1 mmol) in dichloromethane (82 mL) at 0° C. was added DIEA (1.07 mL, 6.1 mmol) and acryloyl chloride (0.36 mL, 4.5 mmol) and the reaction was stirred for 30 mins. LC-MS indicated complete consumption of SM. The reaction mixture was purified by silica gel chromatography to yield tert-butyl (3S,4R)-3-acrylamido-4-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)pyrrolidine-1-carboxylate (1.26 g, 52%). MS (ES+) C28H31Cl2N5O5 requires: 587, found: 588.

Workup

customconsumption of SM
customThe reaction mixture was purified by silica gel chromatography

Sources & evidence

ORD record: ord-93071d7bf7fc46bcaeebebddf0590c01
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434700B2

Reaction notes

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