Triethylamine → HCID 66550744, compound

HRID 1410123Notes

Reaction equation

HRID 1410123 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].CC[N:32]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>C(Cl)Cl>[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]([NH2:32])=[O:22])[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 665513433-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoic acid

Product 1

HCID 66550744HCID 66550744, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoic acid (100 mg, 0.25 mmol), EDCI (70 mg, 0.37 mmol), HOBt (50 mg, 0.37 mmol) and Et3N (49 mg, 0.49 mmol) in DCM (20 mL) was bubbled ammonia until saturation. The mixture was stirred at room temperature for 3 h, then was filtered and the filtrate was concentrated to give residue which was purified by column chromatography (DCM:MeOH=50:1) to afford 3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzamide (22 mg, 14%) as a yellow solid. 1H NMR (300 MHz, DMSO): δ 10.13 (s, 1H), 9.37 (s, 1H), 8.88 (t, 1H, J=1.5 Hz), 8.51 (d, 1H, J=7.8 Hz), 8.10 (s, 1H), 7.98 (d, 1H, J=7.5 Hz), 7.86 (d, 1H, J=2.4 Hz), 7.58 (t, 1H, J=7.8 Hz), 7.49-7.44 (m, 2H), 7.99 (d, 1H, J=8.7 Hz), 3.82 (s, 3H), 3.77 (s, 3H). LC-MS: 408 [M+H]+, tR=1.39 min. HPLC: 97.78% at 214 nm, 97.42% at 254 nm, tR=1.39 min. LC-MS: 408 [M+H]+, tR=1.392 min. HPLC: 95.38% at 214 nm, 96.23% at 254 nm, tR=3.53 min.

Workup

  1. customwas bubbled ammonia until saturation
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated
  4. customto give residue which
  5. customwas purified by column chromatography (DCM:MeOH=50:1)

Sources & evidence

ORD record
ord-3f7be9e8229047168044d59b7f1683ef
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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