Hydrochloric Acid → 3-(4-(1-aminocyclobutyl)phenyl)-8-(1,5-dimethyl-1H-pyrazol-4-yl)-2-phenyl-4H-pyrano[2,3-c]pyridin-4-one hydrochloride

HRID 1037417Notes

Reaction equation

HRID 1037417 reaction equation
[NH2:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[C:13](=[O:36])[C:14]4[C:15]([O:28][C:29]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:16]([C:20]3[C:21](C)=[N:22][N:23]([CH3:26])[C:24]=3[CH3:25])[N:17]=[CH:18][CH:19]=4)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3]1.CN1C(C)=C(C2N=CC=C3C(=O)C(C4C=CC(C5(NC(=O)OC(C)(C)C)CCC5)=CC=4)=C(C4C=CC=CC=4)OC=23)C=N1.[ClH:79]>>[ClH:79].[NH2:1][C:2]1([C:6]2[CH:7]=[CH:8][C:9]([C:12]3[C:13](=[O:36])[C:14]4[C:15]([O:28][C:29]=3[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[C:16]([C:20]3[CH:21]=[N:22][N:23]([CH3:26])[C:24]=3[CH3:25])[N:17]=[CH:18][CH:19]=4)=[CH:10][CH:11]=2)[CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 670678613-(4-(1-aminocyclobutyl)phenyl)-2-phenyl-8-(1,3,5-trimethyl-1H-pyrazol-4-yl)-4H-pyrano[2,3-c]pyridin-4-oneHCID 68227656tert-butyl (1-(4-(8-(1,5-dimethyl-1H-pyrazol-4-yl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate

Product 1

HCID 680548383-(4-(1-aminocyclobutyl)phenyl)-8-(1,5-dimethyl-1H-pyrazol-4-yl)-2-phenyl-4H-pyrano[2,3-c]pyridin-4-one hydrochlorideYield 46%

Procedure

Following the procedure used to prepare 3-(4-(1-aminocyclobutyl)phenyl)-2-phenyl-8-(1,3,5-trimethyl-1H-pyrazol-4-yl)-4H-pyrano[2,3-c]pyridin-4-one, tert-butyl 1-(4-(8-(1,5-dimethyl-1H-pyrazol-4-yl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate was reacted to give the title compound (15 mg, 46%) as an HCl salt. 1H NMR (500 MHz, CD3OD): δ 8.78 (d, J=8.2 Hz, 1H), 8.25 (bs, 1H) 8.15 (d, J=8.3 Hz, 1H), 7.60-7.35 (m, 11H), 3.91 (s, 3H), 2.80-2.78 (m, 2H), 2.65-2.60 (m, 2H), 2.55 (s, 3H), 2.29-2.20 (m, 1H), 2.01-1.91 (m, 1H). LCMS (Method I): RT=4.82 min, [M+F1]+=463.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-09b2b0799541432c806951a26e9c83d4
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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