2-Amino-5-methylbenzenesulfonic acid → 2-{7-[5-Chloro-4-(2-dimethylsulfamoyl-4-methyl-phenylamino)-pyrimidin-2-ylamino]-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl}-n,n-dimethyl-acetamide

HRID 1687425

반응식

HRID 1687425 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1S(O)(=O)=O.ClC([O:16][CH2:17][CH:18]1C2C=CC=CC=2C2C1=CC=CC=2)=O.C1C2C(CO[C:46]([NH:48][C:49]3[CH:54]=CC(C)=CC=3S(O)(=O)=O)=O)C3C(=CC=CC=3)C=2C=CC=1.C1C2C([CH2:73][O:74]C(=O)NC3C=CC(C)=CC=3S(Cl)(=O)=O)C3C(=CC=CC=3)C=2C=CC=1.NC1C=CC(C)=CC=1S([N:100]([CH3:102])[CH3:101])(=O)=O.Cl[C:104]1[N:109]=[C:108]([NH:110][C:111]2[CH:116]=[CH:115][C:114]([CH3:117])=[CH:113][C:112]=2[S:118]([N:121]([CH3:123])[CH3:122])(=[O:120])=[O:119])[C:107]([Cl:124])=[CH:106][N:105]=1>>[Cl:124][C:107]1[C:108]([NH:110][C:111]2[CH:116]=[CH:115][C:114]([CH3:117])=[CH:113][C:112]=2[S:118](=[O:120])(=[O:119])[N:121]([CH3:123])[CH3:122])=[N:109][C:104]([NH:1][C:2]2[C:3]([O:74][CH3:73])=[CH:4][C:5]3[CH2:8][CH2:46][N:48]([CH2:18][C:17]([N:100]([CH3:102])[CH3:101])=[O:16])[CH2:49][CH2:54][C:6]=3[CH:7]=2)=[N:105][CH:106]=1

참가 물질

7

반응물 6

HCID 69342-Amino-5-methylbenzenesulfonic acidHCID 343679-Fluorenylmethyl chloroformateHCID 672635782-Amino-5,n,n-trimethyl-benzenesulfonamideHCID 87330227(2-Chlorosulfonyl-4-methyl-phenyl)-carbamic acid 9H-fluoren-9-ylmethylesterHCID 873302912-(2,5-Dichloro-pyrimidin-4-ylamino)-5,n,n-trimethyl-benzenesulfonamideHCID 873303132-(9h-Fluoren-9-ylmethoxycarbonylamino)-5-methyl-benzenesulfonic acid

생성물 1

HCID 668305582-{7-[5-Chloro-4-(2-dimethylsulfamoyl-4-methyl-phenylamino)-pyrimidin-2-ylamino]-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl}-n,n-dimethyl-acetamide

실험 절차

2-Amino-5-methyl-benzenesulfonic acid using 9-Fluorenylmethyl chloroformate was converted in an analogous manner to Example 820a, to 2-(9H-Fluoren-9-ylmethoxycarbonylamino)-5-methyl-benzenesulfonic acid, which was converted in an analogous manner to Example 820b, to (2-Chlorosulfonyl-4-methyl-phenyl)-carbamic acid 9H-fluoren-9-ylmethylester, which was converted in an analogous manner to Example 820c, to 2-Amino-5,N,N-trimethyl-benzenesulfonamide, which was converted, in an analogous procedure to Example 1d, to 2-(2,5-Dichloro-pyrimidin-4-ylamino)-5,N,N-trimethyl-benzenesulfonamide, which was converted to the title compound in an analogous manner to Example 61e using 2-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethyl-acetamide. Product isolated as a tan foam (0.027 g, 27%). MP: 67-79° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 9.13 (s, 1H), 8.32 (d, 1H, J=8.3 Hz), 8.11 (s, 1H), 7.98 (s, 1H), 7.69-7.67 (m, 1H), 7.48 (m, 1H), 7.39-7.34 (m, 1H), 6.64 (s, 1H), 3.86 (s, 3H), 3.30 (s, 2H), 3.14 (s, 3H), 2.98 (s, 3H), 2.91-2.86 (m, 2H), 2.76-2.64 (m, 12H), 2.41 (s, 3H). MS: 602.48 (MH)+.

출처 및 근거

ORD 기록
ord-2a165a0feb404a4ea534a5cac4755143
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148391B2

연결된 노트

불러오는 중…