1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(2,6-Dichlorophenyl)-1H-indole-6-carboxylic acid thiazolo[5,4-b]pyridin-2-ylamide

HRID 1514946Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([C:18]([OH:20])=O)[CH:12]=2.[N:21]1[C:29]2[C:24](=[N:25][CH:26]=[CH:27][CH:28]=2)[S:23][C:22]=1[NH2:30].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[N:21]1[C:29]2[C:24](=[N:25][CH:26]=[CH:27][CH:28]=2)[S:23][C:22]=1[NH:30][C:18]([C:13]1[CH:12]=[C:11]2[C:16]([CH:17]=[C:9]([C:3]3[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[NH:10]2)=[CH:15][CH:14]=1)=[O:20]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2-(2,6-dichlorophenyl)-1H-indole-6-carboxylic acid (362 mg, 1.18 mmol), thiazolo[5,4-b]pyridin-2-ylamine (179 mg, 1.18 mmol), EDCI (340 mg, 1.77 mmol) and HOBT (176 mg, 1.30 mmol) in THF (10 mL) was heated in a microwave apparatus at 150° C. for 3 h. The insolubles were filtered off and the filtrate was concentrated under reduced pressure. The residue was chromatographed using a 30-70% gradient of heptane/ethyl acetate to afford the title compound. 1H NMR (DMSO-d6, 400 MHz): δ 12.95 (s, broad, 1H), 12.00 (s, broad, 1H), 8.51 (dd, J=4.7, 1.4 Hz, 1H), 8.34 (s, 1H), 8.16 (d, J=7.7 Hz, 1H), 7.88 (dd, J=8.5, 1.4 Hz, 1H), 7.76 (d, J=8.5 Hz, 1H), 7.68 (d, J=8.3 Hz, 2H), 7.54 (m, 2H), 6.66 (m, 1H). MS (m/z) 439.0 (M+1), Retention time=1.41 min (Method 10). Anal. Calcd.: C, 57.41; H, 2.75; N, 12.75. Found: C, 57.29; H, 2.73; N, 12.54.

Workup

filtrationThe insolubles were filtered off
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was chromatographed

Sources & evidence

ORD record: ord-c4f33de1b27f4e9baefcae59351383d7
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222248B2

Reaction notes

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