Triethylamine → HCID 66550545, compound

HRID 1410120Notes

Reaction equation

HRID 1410120 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:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=3)[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:26]=[CH:25][C:21]([C:22]([NH2:32])=[O:23])=[CH:20][CH:19]=3)[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 68379355HCID 68379355, compound

Product 1

HCID 66550545HCID 66550545, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoic acid (210 mg, 0.52 mmol), EDCI (147 mg, 0.77 mmol), HOBt (104 mg, 0.77 mmol) and Et3N (104 mg, 1.07 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 4-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzamide (38 mg, 22%) as a yellow solid. 1H NMR (300 MHz, DMSO): δ 9.14 (s, 1H), 8.30 (s, 1H), 8.27 (s, 1H), 7.87 (s, 1H), 7.84 (s, 1H), 7.62 (d, 1H, J=2.4 Hz), 7.32-7.28 (m, 1H), 6.92 (d, 1H, J=9.0 Hz), 3.75 (s, 3H), 3.72 (s, 3H). LC-MS: 599 [M+H]+, tR=1.54 min. HPLC: 95.59% at 214 nm, 95.99% at 254 nm, tR=4.594 min. LC-MS: 408 [M+H]+, tR=1.392 min. HPLC: 95.38% at 214 nm, 96.23% at 254 nm, tR=5.259 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-6c22337cd9d24402adb7512729b6ab43
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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