Acetic Acid → 3-(3-Chloro-4-methoxy-benzylamino)-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1602245노트

반응식

HRID 1602245 반응식
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[NH:4][N:3]=1.C(O)(=O)C.[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH:27]=O.[BH3-]C#N.[Na+]>CO.CN1C(=O)N(C)CC1>[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH2:27][NH:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[NH:4][N:3]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 786193-Chloro-4-methoxybenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178509242HCID 178509242, 화합물

생성물 1

HCID 196105503-(3-Chloro-4-methoxy-benzylamino)-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine

시약·촉매·용매 2

HCID 887Methanol용매HCID 66611,3-Dimethyl-2-imidazolidinone용매

실험 절차

Analogously to Example 21, 1.00 mmol of 3-amino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine in 26 ml of methanol, 13 ml of DMEU and 3.0 mmol of acetic acid are first reacted with 3-chloro-4-methoxy-benzaldehyde and then reduced with 7.00 mmol of NaCNBH3 (5-7 days). 3-(3-Chloro-4-methoxy-benzylamino)-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine is obtained; m.p. 205-208° C.; HPLC: TRet (Grad20-100)=12.2.

출처 및 근거

ORD 기록
ord-9803bff3c783425c808218ddbf3b0f95
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05981533

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