1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 71279700, 화합물

HRID 246589

반응식

HRID 246589 반응식
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([C:21](O)=[O:22])=[CH:19][NH:18][C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.[F:24][C:25]([F:31])([F:30])[C:26]([CH3:29])([NH2:28])[CH3:27].CCN=C=NCCCN(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([C:21]([NH:28][C:26]([CH3:29])([CH3:27])[C:25]([F:31])([F:30])[F:24])=[O:22])=[CH:19][NH:18][C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 112751881,1,1-Trifluoro-2-methylpropan-2-amineHCID 71280096HCID 71280096, 화합물

생성물 1

HCID 71279700HCID 71279700, 화합물수율 16%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (0.07 g, 0.3 mmol), 1,1,1-trifluoro-2-methylpropan-2-amine (0.05 g, 0.39 mmol), EDCI (0.057 g, 0.3 mmol), DMAP (0.037 g, 0.3 mmol), HATU (0.114 g, 0.3 mmol) and DIPEA (0.163 g, 1.26 mmol) in 10 mL of DMF were stirred at room temperature overnight. The solvent was removed under reduced pressure at 70° C. The residue was triturated with water and then purified by preparative-HPLC (Gemini 5u C18 150×21.2 mm; inject volume: 3 mL/inj, flow rate: 20 mL/min; wavelength: 214 nm and 254 nm; the gradient conditions were: 55% acetonitrile/45% water (0.1% trifluoroacetic acid, v/v) initially, proceeding to 80% acetonitrile/20% water (0.1% trifluoroacetic acid, v/v) in a linear fashion over 9 min.) to give 2-(6-chloro-1-methyl-1H-indazol-3-yl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (0.015 g, 16%) as a white solid. MS: (M+H)+=437; 1H NMR (300 MHz, DMSO): δ 13.03 (s, 1H), 9.10 (s, 1H), 8.53-8.82 (m, 1H), 8.42 (d, 1H, J=8.4 Hz), 8.14 (s, 1H), 8.39 (s, 1H), 7.28 (d, 1H, J=8.7 Hz), 4.20 (s, 3H), 1.77 (s, 6H).

후처리

  1. customThe solvent was removed under reduced pressure at 70° C
  2. customThe residue was triturated with water
  3. custompurified by preparative-HPLC (Gemini 5u C18 150×21.2 mm
  4. wait55% acetonitrile/45% water (0.1% trifluoroacetic acid, v/v) initially, proceeding to 80% acetonitrile/20% water (0.1% trifluoroacetic acid, v/v) in a linear fashion over 9 min.

출처 및 근거

ORD 기록
ord-80b06cc6976c44daa10c3fd64ff836d7
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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