Sodium Acetate → HCID 90404228, compound

HRID 924241Notes

Reaction equation

HRID 924241 reaction equation
[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:16]=[C:17]([CH2:21][CH2:22][CH2:23][NH2:24])[CH:18]=[CH:19][CH:20]=3)=[N:11]2)=[CH:6][CH:5]=1.[CH3:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:38][CH2:39][CH3:40])=[C:32]([NH:34][C:35]([NH2:37])=[S:36])[CH:33]=1.[C:41]([O-])(=[O:43])C.[Na+]>>[CH3:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:38][CH2:39][CH3:40])=[C:32]([NH:34][C:35]([NH:37][C:41]([NH:24][CH2:23][CH2:22][CH2:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([C:12]3[N:13]=[CH:14][N:10]([C:7]4[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:25])[F:26])=[CH:9][CH:8]=4)[N:11]=3)[CH:16]=2)=[O:43])=[S:36])[CH:33]=1

Participants

4

Reactant 3

HCID 517045Sodium AcetateHCID 904043433-(3-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-1-amineHCID 90405349HCID 90405349, compound

Product 1

HCID 90404228HCID 90404228, compound

Procedure

The title compound was prepared as described in Example 63 using 3-(3-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-1-amine (CA18) and 1-(5-methyl-2-propylphenyl)thiourea (CA38). Sodium acetate was used in place of sodium bicarbonate. The title compound was isolated as a white solid (0.134 g, 40%): 1H NMR (400 MHz, DMSO-d6) δ 12.01 (s, 1H), 10.04 (s, 1H), 9.40 (s, 1H), 8.14-8.04 (m, 2H), 8.03-7.92 (m, 2H), 7.68-7.57 (m, 2H), 7.45 (t, J=7.6 Hz, 1H), 7.42-7.32 (m, 2H), 7.11 (t, J=7.1 Hz, 2H), 7.01 (ddd, J=7.9, 1.7, 0.8 Hz, 1H), 3.18 (q, J=6.5 Hz, 2H), 2.73 (dd, J=8.7, 6.6 Hz, 2H), 2.45 (dd, J=8.6, 6.6 Hz, 2H), 2.26 (s, 3H), 1.91-1.75 (m, 2H), 1.55-1.41 (m, 2H), 0.84 (t, J=7.3 Hz, 3H); 19F NMR (376 MHz, DMSO-d6) δ −56.98; ESIMS m/z 597 ([M+H]+), 595 ([M−H]−).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-d59e0062051e47f9941579a855d2fcf6
Source dataset
uspto-grants-2016_03
Patent number
US09278964B2

Reaction notes

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