Dimethylamine → HCID 68283781, compound

HRID 1527558Notes

Reaction equation

[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH2:14][CH2:15]OS(C)(=O)=O)=[CH:10][CH:11]=2)[C:6]([CH2:21][C:22]([N:24]2[C@H:29]([C:30](=[O:41])[NH:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[C:34]=3[F:40])[CH2:28][C@@H:27]3[C@H:25]2[CH2:26]3)=[O:23])=[CH:5]1)(=[O:3])[NH2:2].[CH3:42][NH:43][CH3:44]>CCO>[Cl:39][C:35]1[C:34]([F:40])=[C:33]([CH:38]=[CH:37][CH:36]=1)[CH2:32][NH:31][C:30]([C@@H:29]1[CH2:28][C@@H:27]2[C@@H:25]([CH2:26]2)[N:24]1[C:22](=[O:23])[CH2:21][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH2:15][N:43]([CH3:44])[CH3:42])[CH:8]=2)[N:4]([C:1]([NH2:2])=[O:3])[CH:5]=1)=[O:41]

Participants

Conditions

Temperature: 70 °C

Procedure

Methanesulfonic acid 2-(1-carbamoyl-3-{2-[(1R,3S,5R)-3-(3-chloro-2-fluoro-benzylcarbamoyl)-2-aza-bicyclo[3.1.0]hex-2-yl]-2-oxo-ethyl}-1H-indol-5-yloxy)-ethyl ester in a solution of dimethylamine 5.6 M in EtOH (1 mL) was sealed in a microwave vial and heated at 70° C. for 2 h (Emrys Optimizer; personal chemistry). The reaction mixture was quenched by addition of saturated aqueous NaHCO3, extracted with EtOAc, dried (Na2SO4) and evaporated in vacuo. Then crude residue was purified by catch-release (SCX Tosic Acid-1 g from Silicycle; eluent MeOH (10 mL) to 2M ammonia in MeOH (10 mL)) to give the desired material which was precipitated in Et2O. MS (UPLC/MS): 556.5/558.5 [M+H]+, 600.4/602.5 [M+HCOO]−; tR (HPLC conditions f): 1.46 min.

Workup

customThe reaction mixture was quenched by addition of saturated aqueous NaHCO3
extractionextracted with EtOAc
dry with materialdried (Na2SO4)
customevaporated in vacuo
customThen crude residue was purified by catch-release (SCX Tosic Acid-1 g from Silicycle; eluent MeOH (10 mL) to 2M ammonia in MeOH (10 mL))

Sources & evidence

ORD record: ord-7e7deef0716848378c64a819e8d9cd49
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085555B2

Reaction notes

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