3-[5-(Trifluoroacetyl)thiophen-2-yl]benzoic Acid → N-((4-(4-Phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methyl)-3-(5-(2,2,2-trifluoroacetyl)thiophen-2-yl)benzamide

HRID 1397440Notes

Reaction equation

HRID 1397440 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:12]3([CH2:18][NH2:19])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:20][C:21]([F:39])([F:38])[C:22]([C:24]1[S:28][C:27]([C:29]2[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=2)[C:32](O)=[O:33])=[CH:26][CH:25]=1)=[O:23]>>[C:1]1([C:7]2[N:8]=[C:9]([C:12]3([CH2:18][NH:19][C:32](=[O:33])[C:31]4[CH:35]=[CH:36][CH:37]=[C:29]([C:27]5[S:28][C:24]([C:22](=[O:23])[C:21]([F:20])([F:38])[F:39])=[CH:25][CH:26]=5)[CH:30]=4)[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)[S:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 248966243-[5-(Trifluoroacetyl)thiophen-2-yl]benzoic AcidHCID 67322930(4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine

Product 1

HCID 69950470N-((4-(4-Phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methyl)-3-(5-(2,2,2-trifluoroacetyl)thiophen-2-yl)benzamideYield 15%

Procedure

This compound was synthesized from (4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine and 3-(5-(2,2,2-trifluoroacetyl)thiophen-2-yl)benzoic acid as described in example 118 step 3 (0.022 g, yield 15%). 1H NMR (400 MHz, DMSO) δ 8.650-8.681 (t, 1H), δ 8.132 (s, 2H), δ 8.071 (s, 1H), δ 7.973-7.991 (d, 1H), δ 7.897-7.915 (d, 1H), 7.826-7.846 (d, 1H), 7.786-7.797 (d, 1H), 7.532-7.571 (t, 1H), 7.320-7.357 (t, 2H), 7.254-7.272 (d, 1H), 3.814-3.843 (d 2H), 3.553-3.568 (d, 2H), 3.282-3.409 (d, 2H), 2.22-2.26 (d, 2H), 1.936-2.006 (m, 2H); MS (ESI+) m/z 555.1 (M−H).

Sources & evidence

ORD record
ord-174647f1db534c18b65b435fb1609361
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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