L-Prolinol → 3-(3,4-difluorophenyl)-N-((S)-1-((S)-2-(hydroxymethyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)-6,7-dihydropyrano[4,3-c]pyrazole-1(4H)-carboxamide

HRID 242504Notes

Reaction equation

C(CCN[C:6](=[O:32])[C@@H:7]([NH:12][C:13]([N:15]1[C:19]2[CH2:20][CH2:21][O:22][CH2:23][C:18]=2[C:17]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[C:26]([F:31])[CH:25]=2)=[N:16]1)=[O:14])[C:8]([CH3:11])([CH3:10])[CH3:9])#N.[NH:33]1[CH2:39][CH2:38][CH2:37][C@H:34]1[CH2:35][OH:36]>>[F:31][C:26]1[CH:25]=[C:24]([C:17]2[C:18]3[CH2:23][O:22][CH2:21][CH2:20][C:19]=3[N:15]([C:13]([NH:12][C@@H:7]([C:8]([CH3:9])([CH3:10])[CH3:11])[C:6]([N:33]3[CH2:39][CH2:38][CH2:37][C@H:34]3[CH2:35][OH:36])=[O:32])=[O:14])[N:16]=2)[CH:29]=[CH:28][C:27]=1[F:30]

Participants

Reactant 2

HCID 640091L-Prolinol

HCID 46862252(S)-N-(1-(2-cyanoethylamino)-3,3-dimethyl-1-oxobutan-2-yl)-3-(3,4-difluorophenyl)-6,7-dihydropyrano[4,3-c]pyrazole-1(4H)-carboxamide

Product 1

HCID 585043343-(3,4-difluorophenyl)-N-((S)-1-((S)-2-(hydroxymethyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)-6,7-dihydropyrano[4,3-c]pyrazole-1(4H)-carboxamide

Procedure

Compound 109 was prepared by the procedure described for the synthesis of compound 104 by replacing 2-cyanoethylamine with L-prolinol. LCMS (+ESI) m/z=477.3 [M+H]+. 1H NMR (CDCl3) δ 7.88 (d, J=9.7 Hz, 1H), 7.45-7.51 (m, 1H), 7.30-7.32 (m, 1H), 7.19-7.26 (m, 1H), 4.82 (s, 2H), 4.64 (d, J=9.8 Hz, 1H), 4.45 (br, 1H), 4.29-4.33 (m, 1H), 3.91-3.97 (m, 3H), 3.55-3.74 (m, 3H), 3.18 (br, 2H), 1.86-2.11 (m, 3H), 1.59-1.66 (m, 1H), 1.11 (s, 9H).

Sources & evidence

ORD record: ord-dc7dfaa83ca94fa4aa21af5aa1f0e7df
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653127B2

Reaction notes

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