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

HRID 539324Notes

Reaction equation

HRID 539324 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 or 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, 2 H), 2.23 (s, 3 H), 2.47 (s, 3 H), 4.39 (m, 2 H), 6.55 (s, 2 H), 6.73 (d, 1 H), 6.78 (d, 1 H), 6.86 (dd, 1 H), 7.50 (dd, 1 H), 7.73 (d, 1 H), 9.86 (s, 1 H); MS (ES+) m/z 355 [M+H]+.

Sources & evidence

ORD record
ord-316fb0c662b0457683f87c1eb6d106f7
Source dataset
uspto-grants-2014_10
Patent number
US08865911B2

Reaction notes

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