Ammonia → HCID 178452620, compound

HRID 2170178Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1([C:12]([NH:14][N:15]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]2[C:21]([O:23]C)=O)=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH3:25]>O.CCOC(C)=O>[Cl:20][C:17]1[CH:18]=[CH:19][N:15]2[C:16]=1[C:21]([OH:23])=[N:25][C:12]([C:9]1([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:11][CH2:10]1)=[N:14]2

Participants

Conditions

Temperature: 110 °C

Procedure

A stirred solution of methyl 1-(1-((tert-butoxycarbonyl)amino)cyclopropanecarboxamido)-3-chloro-1H-pyrrole-2-carboxylate (500 mg, 1.40 mmol) in water (12 mL) was purged with NH3 gas for 5 minutes. The sealed pressure tube was heated at 110° C. for 12 h. The reaction mixture was dissolved in EtOAc (100 mL) and washed with water (50 mL). The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified using CombiFlash ISCO (REDISEP®, SiO2, 12 g, 50% EtOAc/petroleum ether) to give tert-butyl (1-(5-chloro-4-hydroxypyrrolo[2,1-f][1,2,4]triazin-2-yl)cyclopropyl)carbamate (210 mg, 46.3%) as a off-white solid. LCMS Condition B-16: retention time 0.91 min, [M+1]=325.1. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.06-1.10 (m, 2H), 1.37-1.45 (m, 2H), 1.41 (s, 9H), 6.57 (d, J=2.4 Hz, 1H), 7.31 (br s, 1H), 7.51 (d, J=2.4 Hz, 1H), 11.32 (br s, 1H).

Workup

washwashed with water (50 mL)
customThe organic layer was separated
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customThe residue was purified

Sources & evidence

ORD record: ord-1cbd4e211c6f4f7c91f803bf62f289a0
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09050345B2

Reaction notes

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