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Water → (1S,4R)-4-[3-(4-Aza-spiro[2.5]oct-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-ylamine

HRID 1402414
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인쇄 미리보기

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HRID 1402414 반응식
[NH2:1][C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@H:5]([OH:12])[CH2:4][CH2:3]1.[H-].[Na+].[CH2:15]1[C:17]2([CH2:22][CH2:21][CH2:20][CH2:19][N:18]2[C:23]2[N:27]3[CH:28]=[C:29](F)[CH:30]=[CH:31][C:26]3=[N:25][N:24]=2)[CH2:16]1.O>CN(C=O)C>[CH2:16]1[C:17]2([CH2:22][CH2:21][CH2:20][CH2:19][N:18]2[C:23]2[N:27]3[CH:28]=[C:29]([O:12][C@H:5]4[C:6]5[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=5)[C@@H:2]([NH2:1])[CH2:3][CH2:4]4)[CH:30]=[CH:31][C:26]3=[N:25][N:24]=2)[CH2:15]1
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참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 86686674(1R,4S)-4-Amino-1,2,3,4-tetrahydronaphthalen-1-olHCID 866872653-(4-Aza-spiro[2.5]oct-4-yl)-6-fluoro-[1,2,4]triazolo[4,3-a]pyridine

생성물 1

HCID 86687266(1S,4R)-4-[3-(4-Aza-spiro[2.5]oct-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-ylamine수율 63%

시약·촉매·용매

1
HCID 6228Dimethylformamide용매2회

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온도
60 °C

실험 절차

To an opaque brown solution of Intermediate A (371 mg, 2.28 mmol) in dry DMF (5 mL) under N2 was added sodium hydride (60% dispersion in mineral oil, 273 mg, 6.83 mmol) and the resulting mixture stirred at RT for 30 min. (CARE: gas evolution) A solution of Intermediate 148c (448 mg, 1.82 mmol) in dry DMF (5 mL) was added and the resulting dark brown solution stirred at 60° C. for 1 h. The solution was cooled to RT, then water (0.2 mL) added (CARE: gas evolution) and the mixture concentrated in vacuo. The residue was redissolved in MeOH (10 mL), applied to an SCX-2 cartridge (25 g) and washed with MeOH (100 mL). The product was eluted with 2M NH3 in MeOH (75 mL); concentration in vacuo left a dark brown gum. Flash chromatography (silica 40 g, 4-7% [2M NH3 in MeOH] in DCM) gave the title compound as a pale brown foam (446 mg, 63%). LCMS (Method 3): Rt 2.31 min, m/z 390 [MH+].

후처리

  1. additionwas added
  2. temperatureThe solution was cooled to RT
  3. concentrationthe mixture concentrated in vacuo
  4. dissolutionThe residue was redissolved in MeOH (10 mL)
  5. washwashed with MeOH (100 mL)
  6. washThe product was eluted with 2M NH3 in MeOH (75 mL)
  7. concentrationconcentration in vacuo
  8. waitleft a dark brown gum

출처 및 근거

ORD 기록
ord-41ace8668f9f404b8af5f2cfa3c13a29
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08907094B2

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