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(2-Nitrophenyl)methanamine → n-{2-[5-Chloro-2-(5-methyl-6-oxo-5,6,8,9-tetrahydro-7-oxa-5-aza-benzocyclohepten-2-ylamino)-pyrimidin-4-ylamino]-benzyl}-acetamide

HRID 1041762
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HRID 1041762 반응식
[N+](C1C=CC=CC=1CN)([O-])=O.[C:12]([O:16][C:17](=[O:29])NCC1C=CC=CC=1[N+]([O-])=O)(C)(C)C.C(OC(=O)[NH:36]CC1C=CC=CC=1N)(C)(C)C.C(OC(=O)N[CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=1[NH:60][C:61]1C(Cl)=CN=C(Cl)N=1)(C)(C)C.NCC1C=CC=CC=1NC1C(Cl)=CN=C(Cl)N=1.Cl[C:88]1[N:93]=[C:92]([NH:94][C:95]2[CH:105]=[CH:104][CH:103]=[CH:102][C:96]=2[CH2:97][NH:98][C:99](=[O:101])[CH3:100])[C:91]([Cl:106])=[CH:90][N:89]=1>>[Cl:106][C:91]1[C:92]([NH:94][C:95]2[CH:105]=[CH:104][CH:103]=[CH:102][C:96]=2[CH2:97][NH:98][C:99](=[O:101])[CH3:100])=[N:93][C:88]([NH:36][C:58]2[CH:57]=[CH:56][C:55]3[N:60]([CH3:61])[C:17](=[O:29])[O:16][CH2:12][CH2:53][C:54]=3[CH:59]=2)=[N:89][CH:90]=1
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반응물 6

HCID 423893(2-Nitrophenyl)methanamineHCID 4409487tert-butyl N-[(2-aminophenyl)methyl]carbamate2회HCID 22981248tert-Butyl 2-nitrobenzylcarbamateHCID 87330207[2-(2,5-Dichloro-pyrimidin-4-ylamino)-benzyl]-carbamic acid tert-butyl esterHCID 87330272N-(2-(aminomethyl)phenyl)-2,5-dichloropyrimidin-4-amine2회
HCID 87330301
N-(2-(2,5-dichloropyrimidin-4-ylamino)benzyl)acetamide

생성물 1

HCID 25155915n-{2-[5-Chloro-2-(5-methyl-6-oxo-5,6,8,9-tetrahydro-7-oxa-5-aza-benzocyclohepten-2-ylamino)-pyrimidin-4-ylamino]-benzyl}-acetamide

실험 절차

Following a procedure analogous to Example 1783c, 2-nitro-benzylamine was converted to 2-nitro-benzyl-carbamic acid tert-butyl ester, which following a procedure analogous to Example 1791b was converted to 2-amino-benzyl-carbamic acid tert-butyl ester. Following a procedure analogous to Example 1751b, 2-amino-benzyl-carbamic acid tert-butyl ester was converted to [2-(2,5-dichloro-pyrimidin-4-ylamino)-benzyl]-carbamic acid tert-butyl ester, which following a procedure analogous to Example 1773c was converted to N-(2-(aminomethyl)phenyl)-2,5-dichloropyrimidin-4-amine. Following a procedure analogous to Example 1792a, N-(2-(aminomethyl)phenyl)-2,5-dichloropyrimidin-4-amine was converted to N-(2-(2,5-dichloropyrimidin-4-ylamino)benzyl)acetamide, which following a procedure analogous to Example 1741e was converted to N-{2-[5-chloro-2-(5-methyl-6-oxo-5,6,8,9-tetrahydro-7-oxa-5-aza-benzocyclohepten-2-ylamino)-pyrimidin-4-ylamino]-benzyl}-acetamide. TFA salt: 1H NMR (300 MHz, CD3OD) δ 8.12 (s, 1H), 7.4 (m, 4H), 7.32 (d, 1H), 7.20 (dd, 1H), 7.10 (d, 1H), 4.3 (m, 4H), 3.3 (s, 3H), 2.76 (t, 2H), 1.89 (s, 3H); MS (m/e) 467 (M+1).

출처 및 근거

ORD 기록
ord-38193203e7f24c14bae251df77a2b852
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08552186B2

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