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Formamidine acetate → 4-[4-(4-Fluorophenyl)-1-pyrrolidin-3-yl-1H-imidazol-5-yl]pyrimidine

HRID 1896657
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HRID 1896657 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][N:11]([CH:19]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20]3)[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][N:14]=2)=[CH:4][CH:3]=1.NC1N=C(C2N(C3CCN(C(OC(C)(C)C)=O)C3)C=NC=2C2C=CC(F)=CC=2)C=CN=1.C(O)(=O)C.C(N)=N.FC1C=CC(C2N=CN(C3CCNC3)C=2C2C=CN=C(N)N=2)=CC=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][N:11]([CH:19]3[CH2:23][CH2:22][NH:21][CH2:20]3)[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][N:14]=2)=[CH:4][CH:3]=1
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참가 물질

5

반응물 4

HCID 160693Formamidine acetateHCID 57461720HCID 57461720, 화합물2회HCID 57461721HCID 57461721, 화합물HCID 57461722tert-Butyl 3-[4-(4-fluorophenyl)-5-pyrimidin-4-yl-1H-imidazol-1-yl]pyrrolidine-1-carboxylate

생성물 1

HCID 574617254-[4-(4-Fluorophenyl)-1-pyrrolidin-3-yl-1H-imidazol-5-yl]pyrimidine

실험 절차

tert-Butyl 3-[4-(4-fluorophenyl)-5-pyrimidin-4-yl-1H-imidazol-1-yl]pyrrolidine-1-carboxylate (C19, prepared according to the general procedure for the synthesis of tert-butyl 3-[5-(2-aminopyrimidin-4-yl)-4-(4-fluorophenyl)-1H-imidazol-1-yl]pyrrolidine-1-carboxylate (C17) in Example 7, except that formamidine acetate was used in place of guanidine hydrochloride) was converted to the product using conditions similar to those employed for transformation of tert-butyl 3-[5-(2-aminopyrimidin-4-yl)-4-(4-fluorophenyl)-1H-imidazol-1-yl]pyrrolidine-1-carboxylate (C17) to 4-[4-(4-fluorophenyl)-1-pyrrolidin-3-yl-1H-imidazol-5-yl]pyrimidin-2-amine (C18) in Example 7. The product was obtained as a solid. Yield: 1.58 g, 5.11 mmol, 70%. LCMS m/z 310.4 (M+1). 1H NMR (400 MHz, CD3OD) δ 2.16 (m, 1H), 2.37 (m, 1H), 3.02 (m, 1H), 3.09 (dd, J=12.2, 4.6 Hz, 1H), 3.21 (m, 1H), 3.3 (m, 1H, assumed; obscured by solvent signal), 5.32 (m, 1H), 7.09 (dd, J=8.6, 8.6 Hz, 2H), 7.26 (d, J=5.2 Hz, 1H), 7.38 (dd, J=8.3, 5.5 Hz, 2H), 8.15 (s, 1H), 8.63 (d, J=5.5 Hz, 1H), 9.28 (s, 1H).

후처리

  1. customThe product was obtained as a solid

출처 및 근거

ORD 기록
ord-f9e9f4b0b379441494a53aab961fc34e
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08518944B2

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