Triethylamine → HCID 178508420, 화합물

HRID 2173705노트

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HRID 2173705 반응식
[NH2:1][C:2]1[C:3]([C:13]([OH:15])=O)=[N:4][C:5]([Br:12])=[C:6]([C:8]([F:11])([F:10])[F:9])[N:7]=1.CCN(CC)CC.[F:23][C:24]([F:32])([F:31])[C:25]1[CH:29]=[C:28]([NH2:30])[NH:27][N:26]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN1C(=O)CCC1>[F:23][C:24]([F:32])([F:31])[C:25]1[CH:29]=[C:28]([NH:30][C:13]([C:3]2[C:2]([NH2:1])=[N:7][C:6]([C:8]([F:9])([F:10])[F:11])=[C:5]([Br:12])[N:4]=2)=[O:15])[NH:27][N:26]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 584422963-Amino-6-bromo-5-trifluoromethyl-pyrazine-2-carboxylic acid2회HCID 178507669HCID 178507669, 화합물

생성물 1

HCID 178508420HCID 178508420, 화합물

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

To a stirred solution of 3-amino-6-bromo-5-trifluoromethyl-pyrazine-2-carboxylic acid (Intermediate 2) (100 mg, 0.350 mmol) in dry NMP (2 ml) was added NEt3 (0.097 ml, 0.699 mmol) followed by 3-(trifluoromethyl)-1H-pyrazol-5-amine (48.0 mg, 0.318 mmol). The mixture was stirred at RT for 5 minutes, before treating with HATU (133 mg, 0.350 mmol). The resulting orange solution was stirred at RT for 10 minutes and then partitioned between EtOAc (50 ml) and 1M NaOH (30 ml). The organic portion was separated and washed with 1M NaOH (20 ml), water (20 ml), dried (MgSO4) and concentrated in vacuo. Purification of the crude residue by chromatography on silica eluting with iso-hexane/EtOAc (gradient of 0 to 50% EtOAc) afforded the title compound as a yellow solid.

후처리

  1. stirringThe resulting orange solution was stirred at RT for 10 minutes
  2. custompartitioned between EtOAc (50 ml) and 1M NaOH (30 ml)
  3. customThe organic portion was separated
  4. washwashed with 1M NaOH (20 ml), water (20 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customPurification of the crude residue by chromatography on silica eluting with iso-hexane/EtOAc (gradient of 0 to 50% EtOAc)

출처 및 근거

ORD 기록
ord-286af4ac62094de495c699db7d9039e1
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056867B2

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