5-Methylthiophene-2-carboxylic acid → HCID 57385114, compound

HRID 1770935Notes

Reaction equation

HRID 1770935 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.[CH3:10][C:11]1[C:12]([NH2:26])=[N:13][C:14]2([C:24]3[C:19](=[CH:20][CH:21]=[C:22]([NH2:25])[CH:23]=3)[O:18][CH2:17][CH2:16]2)[N:15]=1>>[NH2:26][C:12]1[C:11]([CH3:10])=[N:15][C:14]2([C:24]3[C:19](=[CH:20][CH:21]=[C:22]([NH:25][C:7]([C:5]4[S:6][C:2]([CH3:1])=[CH:3][CH:4]=4)=[O:9])[CH:23]=3)[O:18][CH2:17][CH2:16]2)[N:13]=1

Participants

3

Reactant 2

HCID 747135-Methylthiophene-2-carboxylic acidHCID 679794075'-Methylspiro[chromane-4,2'-imidazole]-4',6-diamine2×

Product 1

HCID 57385114HCID 57385114, compoundYield 57%

Procedure

The title compound (45.5 mg, 57% yield) was prepared as described for Example 13a starting from 5-methylthiophene-2-carboxylic acid (32.1 mg, 0.23 mmol) and 5′-methylspiro[chroman-4,2′-imidazole]-4′,6-diamine (Intermediate 30, 52 mg, 0.23 mmol): 1H NMR (500 MHz, DMSO-d6) δ ppm 1.91 (m, 2H), 2.23 (s, 3H), 2.47 (s, 3H), 4.39 (m, 2H), 6.55 (s, 2H), 6.73 (d, 1H), 6.78 (d, 1H), 6.86 (dd, 1H), 7.50 (dd, 1H), 7.73 (d, 1H), 9.86 (s, 1H); MS (ES+) m/z 355 [M+H]+.

Sources & evidence

ORD record
ord-87e83b320138485abcdd14c4b4ab020f
Source dataset
uspto-grants-2016_02
Patent number
US09248129B2

Reaction notes

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