Ammonia → HCID 136359929, compound

HRID 1969672Notes

Reaction equation

[CH2:1]([CH:3]1[CH:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][NH:17][C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[CH2:6][CH:5]([CH2:20][CH2:21][CH2:22][C:23](OCC)=[O:24])[CH2:4]1)[CH3:2].[NH3:28]>>[CH2:1]([C@H:3]1[C@@H:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][NH:17][C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[CH2:6][CH:5]([CH2:20][CH2:21][CH2:22][C:23]([NH2:28])=[O:24])[CH2:4]1)[CH3:2]

Participants

Reactant 2

HCID 222Ammonia

HCID 136009502HCID 136009502, compound

Product 1

HCID 136359929HCID 136359929, compoundYield 100.2%

Conditions

Temperature: 85 °C

Procedure

Ethyl 4-(3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)butanoate (0.080 g, 0.217 mmol, prepared using III from Preparation #25 and (E)-ethyl 4-(diethoxyphosphoryl)but-2-enoate, W) and ammonia (7 N in MeOH, 6.2 mL, 43.3 mmol). The reaction vessel was sealed and heated to about 85° C. After about 2 days the tube was cooled to rt and the reaction mixture was concd in vacuo to provide 4-((3R,4S)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)butanamide (0.074 g, 100%) as a solid which was used without further purification: LC/MS (Table 1, Method c) Rt=0.50 min.; MS m/z: 341 (M+H)+.

Workup

customThe reaction vessel was sealed
temperatureAfter about 2 days the tube was cooled to rt

Sources & evidence

ORD record: ord-60babba8a2cf4faf9bf26ca6b85dc856
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426411B2

Reaction notes

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