4-(4-Chloro-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoic acid → 4-(4-Chloro-3-(dibutylcarbamoyl)-1H-pyrazol-1-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoic acid

HRID 528927Notes

Reaction equation

HRID 528927 reaction equation
[Cl:1][C:2]1[C:3]([C:29](=[O:39])[N:30]([CH2:35][CH2:36][CH2:37][CH3:38])[CH2:31][CH2:32][CH2:33][CH3:34])=[N:4][N:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=2[C:17]([N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20]2)=[O:18])[C:6]=1C.ClC1C(C(=O)N(CCCC)CCCC)=NN(C2C=CC(C(OCC)=O)=CC=2C(N2CCC3C(=CC=CC=3)C2)=O)C=1>>[Cl:1][C:2]1[C:3]([C:29](=[O:39])[N:30]([CH2:35][CH2:36][CH2:37][CH3:38])[CH2:31][CH2:32][CH2:33][CH3:34])=[N:4][N:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=2[C:17]([N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20]2)=[O:18])[CH:6]=1

Participants

3

Reactant 2

HCID 710621944-(4-Chloro-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoic acidHCID 71062365Ethyl 4-(4-chloro-3-(dibutylcarbamoyl)-1H-pyrazol-1-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate

Product 1

HCID 710625694-(4-Chloro-3-(dibutylcarbamoyl)-1H-pyrazol-1-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoic acidYield 94%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 1F, ethyl 4-(4-chloro-3-(dibutylcarbamoyl)-1H-pyrazol-1-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (155 mg, 0.27 mmol) was converted to the title compound (138 mg, 94%). MS(ESI+) m/z 537.3 (M+H)+.

Sources & evidence

ORD record
ord-a6200788798e4013ad651688c274df6e
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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