HCID 53411827, compound → HCID 59636653, compound

HRID 2098209Notes

Reaction equation

HRID 2098209 reaction equation
[NH2:1][C:2]1[S:6][CH:5]=[C:4]([C:7]#[N:8])[C:3]=1[C:9]1[CH:14]=[N:13][CH:12]=[CH:11][N:10]=1.Cl.[N:16]1[C:25]2[C:20](=[C:21]([CH2:26][C:27](O)=[O:28])[CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1>>[C:7]([C:4]1[C:3]([C:9]2[CH:14]=[N:13][CH:12]=[CH:11][N:10]=2)=[C:2]([NH:1][C:27](=[O:28])[CH2:26][C:21]2[CH:22]=[CH:23][CH:24]=[C:25]3[C:20]=2[CH:19]=[CH:18][CH:17]=[N:16]3)[S:6][CH:5]=1)#[N:8]

Participants

3

Reactant 2

HCID 53411827HCID 53411827, compoundHCID 68754904HCID 68754904, compound

Product 1

HCID 59636653HCID 59636653, compound

Procedure

The title compound was synthesized from 5-amino-4-(pyrazin-2-yl)thiophene-3-carbonitrile (30.5 mg, 0.15 mmol) and 2-(quinolin-5-yl)acetic acid hydrochloride (36 mg, 0.16 mmol) according to protocol A. The product was purified by HPLC method [4], retention time=1.393 min; MS (ESI) 372.1 (MH+); 1H NMR (300 MHz, CD3OD) δ 9.30 (d, J=1.5 Hz, 1H), 9.06 (dd, J=4.8, 1.3 Hz, 1H), 8.99 (d, J=8.5 Hz, 1H), 8.51 (d, J=2.6 Hz, 1H), 8.29 (t, J=1.9 Hz, 1H), 8.20 (d, J=8.6 Hz, 1H), 8.09 (dd, J=8.6, 7.1 Hz, 1H), 7.95 (s, 1H), 7.93 (d, J=6.7 Hz, 1H), 7.86 (dd, J=8.6, 4.9 Hz, 1H), 4.55 (s, 2H).

Workup

  1. customThe product was purified by HPLC method [4], retention time=1.393 min

Sources & evidence

ORD record
ord-d6151850ef5a4a1cb2d0f27cef380c70
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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