Hydrazine hydrate (1:1) → 4-(2-(1-Methylpyrrolidin-2-yl)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amine

HRID 1917164노트

반응식

HRID 1917164 반응식
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][S:12][C:11]2[CH:15]=[C:16]([N+:19]([O-])=O)[CH:17]=[CH:18][C:10]1=2.O.NN>CO.[Ni]>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][S:12][C:11]2[CH:15]=[C:16]([NH2:19])[CH:17]=[CH:18][C:10]1=2

참가 물질

5

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 591440834-(2-(1-Methylpyrrolidin-2-yl)ethyl)-7-nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine

생성물 1

HCID 591441084-(2-(1-Methylpyrrolidin-2-yl)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amine

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매

실험 절차

A solution of 4-(2-(1-methylpyrrolidin-2-yl)ethyl)-7-nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine (0.82 g, 2.67 mmol) in methanol (10 mL) under an argon atmosphere was treated with hydrazine hydrate (1.29 mL, 26.7 mmol) and a small amount of Raney Nickel (˜0.15 g, 2.67 mmol). The reaction was transferred to a pre-heated oil bath at 65° C. After 3 hours, the reaction was poured over a pad of Celite, rinsing with methanol. The filtrate was concentrated, and the residue was poured over a pad of silica gel. The silica gel pad was rinsed with 1:9 (2M NH3 in methanol):dichloromethane (200 mL). The filtrate was concentrated, dried under reduced pressure, and carried on to the next step. 1H-NMR (DMSO-d6) δ 6.48 (brd, J=9.3 Hz, 1H), 6.27-6.24 (m, 2H), 4.42 (brs, 2H), 3.33-3.29 (m, 2H), 3.13-3.06 (m, 2H), 2.99-2.96 (m, 2H), 2.96-2.90 (m, 1H), 2.19 (s, 3H), 2.06-1.97 (m, 2H), 1.96-1.78 (m, 2H), 1.63-1.60 (m, 2H), 1.56-1.40 (m, 2H); ESI-MS (m/z, %): 278 (MH+, 100).

후처리

  1. customThe reaction was transferred to a pre-heated oil bath at 65° C
  2. additionthe reaction was poured over a pad of Celite
  3. washrinsing with methanol
  4. concentrationThe filtrate was concentrated
  5. additionthe residue was poured over a pad of silica gel
  6. washThe silica gel pad was rinsed with 1:9 (2M NH3 in methanol)
  7. concentrationThe filtrate was concentrated
  8. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-2a30b3eb6df341b18f369fea3b1b169b
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618286B2

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