Triethylamine → HCID 60205658, 화합물

HRID 875893노트

반응식

HRID 875893 반응식
C(N(CC)CC)C.[Cl:8][C:9]1[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][N:12]=[C:11]2[NH:19][CH:20]=[C:21]([NH2:22])[C:10]=12.[CH3:23][O:24][C@H:25]([CH3:29])[C:26](O)=[O:27].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>ClCCl>[Cl:8][C:9]1[C:14]([C:15]([F:18])([F:16])[F:17])=[CH:13][N:12]=[C:11]2[NH:19][CH:20]=[C:21]([NH:22][C:26](=[O:27])[C@H:25]([O:24][CH3:23])[CH3:29])[C:10]=12

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 2733584(2R)-2-methoxypropanoic acidHCID 602053084-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-amine

생성물 1

HCID 60205658HCID 60205658, 화합물수율 96.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triethylamine (430 mg, 0.592 mL, 4.25 mmol) was slowly added to a mixture of 4-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-amine (200 mg, 0.849 mmol; Example 12, Step G), (R)-2-methoxypropanoic acid (106 mg, 1.02 mmol) and bis(2-oxooxazolidin-3-yl)phosphinic chloride (238 mg, 0.934 mmol) in anhydrous dichloromethane (10 mL). The resulting mixture was stirred at room temperature for 16 hours. The mixture was concentrated, and the residue stirred in THF (5 mL) and treated with water (20 mL). The solid, which separated, was collected by filtration and washed with water then dried under vacuum to yield (R)—N-(4-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methoxypropanamide (263 mg, 96% yield) as a solid. 1H NMR (400 MHz, (CD3)2SO) δ 12.49 (br s, 1H), 9.48 (s, 1H), 8.59 (s, 1H), 7.89 (d, 1H), 3.93 (q, 1H), 3.41 (s, 3H), 1.36 (d, 3H).

후처리

  1. concentrationThe mixture was concentrated
  2. stirringthe residue stirred in THF (5 mL)
  3. additiontreated with water (20 mL)
  4. customThe solid, which separated
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customthen dried under vacuum

출처 및 근거

ORD 기록
ord-3b4427471c854430afe7d0f66302f850
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08981085B2

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