Water → 3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenyl)benzamide

HRID 1410021Notes

Reaction equation

HRID 1410021 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:29]=[CH:28][S:27][C:14]=3[N:15]=[C:16]([C:18]3[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=3)[C:21](O)=[O:22])[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[NH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[O:41][C:40]([SH:42])=[N:39][N:38]=2)=[CH:33][CH:32]=1.CCN=C=NCCCN(C)C.O>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:29]=[CH:28][S:27][C:14]=3[N:15]=[C:16]([C:18]3[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=3)[C:21]([NH:30][C:31]3[CH:32]=[CH:33][C:34]([C:37]4[O:41][C:40]([SH:42])=[N:39][N:38]=4)=[CH:35][CH:36]=3)=[O:22])[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 665513433-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoic acidHCID 178507465HCID 178507465, compound

Product 1

HCID 1364140703-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenyl)benzamideYield 19.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoic acid (100 mg, 0.245 mmol), 5-(4-aminophenyl)-1,3,4-oxadiazole-2-thiol (53 mg, 0.27 mmol), EDCI (94 mg, 0.49 mmol) and DMAP (90 mg, 0.735 mmol) in 5 mL of DMF was stirred at room temperature for 40 hours. The mixture was poured into water and extracted with EtOAc (3×10 mL). The water layer was allowed to stand overnight then filtered to give 3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenyl)benzamide (28 mg, 19.5%) as white solid. 1H NMR (300 MHz, DMSO): δ 10.67 (s, 1H), 10.20 (s, 1H), 9.41 (s, 1H), 8.96 (s, 1H), 9.61 (d, 1H, J=7.8 Hz), 8.10 (d, 1H, J=8.1 Hz), 7.96-7.93 (m, 3H), 7.83-7.68 (m, 4H), 7.55 (d, 1H, J=6.6 Hz), 6.99 (d, 1H, J=9.0 Hz), 3.81 (s, 3H), 3.74 (s, 3H). LC-MS: 584 [M+H]+, 582 [M−H]−, tR=1.61 min. HPLC: 96.43% at 214 nm, 96.83% at 254 nm, tR=4.60 min.

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. waitto stand overnight
  3. filtrationthen filtered

Sources & evidence

ORD record
ord-08b77d110c7546e5952568d6469458ee
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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