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Pivaloyl chloride → HCID 178472060、化合物

HRID 1527139
ノート
印刷プレビュー

反応式

HRID 1527139 の反応式
CCCCCC[O:7][C:8](/[N:10]=[C:11](\[NH2:46])/[C:12]1[CH:13]=[CH:14][C:15]([NH:18][CH2:19][C:20]2[N:28]([CH3:29])[C:27]3[CH:26]=[CH:25][C:24]([C:30]([N:32]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][N:45]=4)[CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:31])=[CH:23][C:22]=3[N:21]=2)=[CH:16][CH:17]=1)=[O:9].NC1C=C(C=CC=1NC)C(N(C1C=CC=CN=1)CCC(OCC)=O)=O.O1C(=O)N=C(C2C=CC(NCC(O)=O)=CC=2)N1.C(Cl)(=O)C(C)(C)C>>[O:7]1[C:8](=[O:9])[N:10]=[C:11]([C:12]2[CH:13]=[CH:14][C:15]([NH:18][CH2:19][C:20]3[N:28]([CH3:29])[C:27]4[CH:26]=[CH:25][C:24]([C:30]([N:32]([C:40]5[CH:41]=[CH:42][CH:43]=[CH:44][N:45]=5)[CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:31])=[CH:23][C:22]=4[N:21]=3)=[CH:16][CH:17]=2)[NH:46]1
参加物実験手順出典と根拠反応ノート

参加物

5

反応物 4

HCID 62493Pivaloyl chlorideHCID 6445226ethyl 3-(2-((4-(N-(hexyloxycarbonyl)carbamimidoyl)phenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoateHCID 11982993N-(3-Amino-4-(methylamino)benzoyl)-N-2-pyridinyl-beta-alanine ethyl ester2 回HCID 1785258632-[4-(5-oxo-2H-1,2,4-oxadiazol-3-yl)anilino]acetic acid2 回

生成物 1

HCID 178472060
HCID 178472060、化合物

実験手順

U.S. Pat. No. 7,202,368 describes an alternative process for the synthesis of dabigatran etexilate (see Scheme 2). Example 3 describes the condensation between ethyl 3-{[3-amino-4-(methylamino)benzoyl](pyridin-2-yl)amino}propanoate (compound II) and 2-[4-(1,2,4-oxadiazol-5-on-3-yl)phenylamino]acetic acid (compound VII) in the presence of a coupling agent such as N,N′-carbonyldiimidazole (CDI), propanephosphonic anhydride (PPA), or pivaloyl chloride, to give ethyl 3-{[(2-{[(4-{1,2,4-oxadiazol-5-on-3-yl}phenyl)amino]methyl}-1-methyl-1H-benzimidazol-5-yl)carbonyl](pyridin-2-yl)amino}propanoate (compound VIII), which is subsequently hydrogenated (Example 4) in the presence of a palladium catalyst to give ethyl 3-{[(2-{[(4-carbamimidoylphenyl)amino]methyl}-1-methyl-1H-benzimidazol-5-yl)carbonyl](pyridin-2-yl)amino}propanoate (compound V). Then, Example 5 describes the acylation of compound V with n-hexyl chloroformate (compound VI) to give dabigatran etexilate. Finally, Example 6 describes the conversion of dabigatran etexilate into its mesylate salt. Although the patent describes the HPLC purities of intermediate compounds II, VII, VIII and V, no information is given neither about the purity of the isolated dabigatran etexilate nor about its mesylate salt.

出典と根拠

ORDレコード
ord-5859b5546d844541a069474e951b578f
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09086390B2

反応ノート

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