HCID 58550625, compound → HCID 67995839, compound

HRID 1890715Notes

Reaction equation

[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@:3]21[CH2:43][C:13]1[CH:14]=[C:15]3[C:20](=[CH:21][C:12]=1[CH2:11]2)[N:19]=[CH:18][C:17]([CH2:22][NH:23][C@H:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:25][CH2:26][NH:27][C:28]1([C:33]([O:35]C)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1)=[CH:16]3.O([Si](C)(C)C)[K:45]>C1COCC1>[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@:3]21[CH2:43][C:13]1[CH:14]=[C:15]3[C:20](=[CH:21][C:12]=1[CH2:11]2)[N:19]=[CH:18][C:17]([CH2:22][NH:23][C@H:24]([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[CH2:25][CH2:26][NH:27][C:28]1([C:33]([O-:35])=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32]1)=[CH:16]3.[K+:45]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methyl 1-{[(3S)-3-({[(7S)-2′-oxo-1′,2′,6,8-tetrahydrospiro[cyclo-penta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridin]-3-yl]methyl}amino)-3-phenylpropyl]amino}cyclopentanecarboxylate from Step A (50. mg, 0.087 mmol) in a minimal amount of THF (5 mL) was added KOTMS (22 mg, 0.17 mmol), prior to heating to 50° C. Additional KOTMS was added as needed (˜2 equiv) until very little starting material was detected in solution. The reaction was allowed to cool to ambient temperature before the THF solution was separated from the precipitated solids. Analysis of the remaining solids indicated it was 87% title compound and 13% starting material. This mixture was used without further purification in the next step. MS: m/z=562 (M+1).

Workup

customwas separated from the precipitated solids
customThis mixture was used without further purification in the next step

Sources & evidence

ORD record: ord-9abbdd16dd2c4f1bb60abdd04945b3f0
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507477B2

Reaction notes

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