Trifluoroacetic acid → HCID 178466700, compound

HRID 502433Notes

Reaction equation

HRID 502433 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[C:16]([O:18][CH2:19][C:20]2[NH:24][N:23]=[N:22][N:21]=2)[CH:17]=1)[C:6]([NH:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=[O:7].C(OC(N1CCC(NC(=O)C2C=C(OCC3N(C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)N=NN=3)C=C(OC)C=2)CC1)=O)(C)(C)C.C(OC(N1CCC(NC(=O)C2C=C(OCC3N=NN(C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)N=3)C=C(OC)C=2)CC1)=O)(C)(C)C.FC(F)(F)C(O)=O.[CH2:132]([O:134][C:135]1[CH:136]=[C:137]([CH:140]=[C:141]([O:144][CH2:145][CH3:146])[C:142]=1[F:143])[CH:138]=O)[CH3:133].C([BH3-])#N.[Na+].C(N(C(C)C)C(C)C)C>ClCCl.C(O)C.C(O)(=O)C>[CH2:132]([O:134][C:135]1[CH:136]=[C:137]([CH:140]=[C:141]([O:144][CH2:145][CH3:146])[C:142]=1[F:143])[CH2:138][N:12]1[CH2:11][CH2:10][CH:9]([NH:8][C:6](=[O:7])[C:5]2[CH:15]=[C:16]([O:18][CH2:19][C:20]3[NH:21][N:22]=[N:23][N:24]=3)[CH:17]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:14][CH2:13]1)[CH3:133]

Participants

11

Reactant 7

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 591282733,5-Diethoxy-4-fluoro-benzaldehydeHCID 684564844-[3-methoxy-5-(1-trityl-1H-tetrazol-5-ylmethoxy)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl esterHCID 684578574-[3-methoxy-5-(2-trityl-2H-tetrazol-5-ylmethoxy)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl esterHCID 178493414HCID 178493414, compound

Product 1

HCID 178466700HCID 178466700, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

In analogy to the procedure described in example 50k), 3-methoxy-N-piperidin-4-yl-5-(1H-tetrazol-5-ylmethoxy)-benzamide [prepared from 4-[3-methoxy-5-(1-trityl-1H-tetrazol-5-ylmethoxy)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester and/or 4-[3-methoxy-5-(2-trityl-2H-tetrazol-5-ylmethoxy)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester by reaction with trifluoroacetic acid in dichloromethane in analogy to the procedure described in example 50i)] was reacted with 3,5-diethoxy-4-fluoro-benzaldehyde (example 50 g), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as off-white solid. MS: 529.2 (MH+).

Sources & evidence

ORD record
ord-c1681fe5717846b1a96f7ca057c07fd9
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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