Hydrochloric Acid → 1-(2-methylpropyl)-2-propyl-2H-pyrazolo[3,4-c][1,8]naphthyridin-4-amine

HRID 1360426노트

반응식

HRID 1360426 반응식
C(OC([NH:8]C1C(B(O)O)=CC=CN=1)=O)(C)(C)C.Cl.C(=O)([O-])[O-].[Na+].[Na+].[CH3:25][CH:26]([CH3:45])[CH2:27][C:28]1[N:29]([CH2:42][CH2:43][CH3:44])[N:30]=[C:31]2[C:40]=1[C:39]1[CH:38]=[CH:37][CH:36]=C[C:34]=1[N:33]=[C:32]2[NH2:41].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)CC.C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:25][CH:26]([CH3:45])[CH2:27][C:28]1[N:29]([CH2:42][CH2:43][CH3:44])[N:30]=[C:31]2[C:40]=1[C:39]1[CH:38]=[CH:37][CH:36]=[N:8][C:34]=1[N:33]=[C:32]2[NH2:41]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 112775352H-Pyrazolo[3,4-c]quinolin-4-amine, 1-(2-methylpropyl)-2-propyl-HCID 22135186(2-[(tert-Butoxycarbonyl)amino]pyridin-3-yl)boronic acid

생성물 1

HCID 577175911-(2-methylpropyl)-2-propyl-2H-pyrazolo[3,4-c][1,8]naphthyridin-4-amine수율 11.2%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 10311-Propanol용매2회HCID 1140Toluene용매

실험 절차

A modification of the method described in Example 16 was used to treat 2-tert-butoxycarbonylamino-3-pyridylboronic acid (11.33 mmol) in 1-propanol (10 mL) with hydrochloric acid (12 mL of 1 M) followed by sodium carbonate (1.99 g, 18.8 mmol), 4-bromo-5-(2-methylpropyl)-1-propyl-1H-pyrazole-3-carbonitrile (1.53 g, 5.66 mmol, prepared as described in Example 1) in 1-propanol (5 mL), triphenylphosphine (44.5 mg, 0.17 mmol), and palladium (II) acetate (13 mg, 0.057 mmol) in toluene (0.25 mL). The reaction was complete after it was heated overnight. Following the work-up procedure and purification, 0.18 g of 1-(2-methylpropyl)-2-propyl-2H-pyrazolo[3,4-c][1,8]naphthyridin-4-amine was obtained as off-white needles, mp 257-260° C.

후처리

  1. temperaturewas heated overnight
  2. customthe work-up procedure and purification

출처 및 근거

ORD 기록
ord-3f706dc259dc4c449ee751bea2076911
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879849B2

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