3-(Benzyloxy)benzoic acid → tert-butyl 5-amino-4-cyano-3-(3-hydroxyphenyl)-1H-pyrazole-1-carboxylate

HRID 1518295Notes

Reaction equation

HRID 1518295 reaction equation
[NH2:1][C:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][C:17](O)=[CH:16][CH:15]=2)[C:3]=1[C:21]#[N:22].C([O:30]C1C=C(C=CC=1)C(O)=O)C1C=CC=CC=1>>[NH2:1][C:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:30])[CH:15]=2)[C:3]=1[C:21]#[N:22]

Participants

3

Reactant 2

HCID 3092263-(Benzyloxy)benzoic acidHCID 136027725tert-butyl 5-amino-4-cyano-3-(4-hydroxyphenyl)-1H-pyrazole-1-carboxylate

Product 1

HCID 59447530tert-butyl 5-amino-4-cyano-3-(3-hydroxyphenyl)-1H-pyrazole-1-carboxylate

Procedure

Compound 36A was prepared in a similar manner to the synthesis of compound 31F by substituting 4-(benzyloxy)benzoic acid with 3-(benzyloxy)benzoic acid: 1H NMR (DMSO-d6): δ 9.70 (s, 1H), 7.68 (s, 2H), 7.25-7.32 (m, 3H), 6.86-6.89 (m, 1H), 1.60 (s, 9H). MS (ESI(+)): m/z 322 (M+Na).

Sources & evidence

ORD record
ord-c7dec6bb0bdc4f3992a07ce39ab2aaec
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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