Trifluoroacetic acid → HCID 10392326, compound

HRID 1294732Notes

Reaction equation

HRID 1294732 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[O:29])=[CH:24][CH:23]=2)[N:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1.[N:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:41]2[CH:48]=[CH:47][C:44]([CH:45]=O)=[CH:43][CH:42]=2)[CH:36]=1.[B][B][B][B][B][B][B][B][B][B].C(O)(C(F)(F)F)=O>>[CH2:33]([N:30]([CH2:31][CH3:32])[C:28](=[O:29])[C:25]1[CH:24]=[CH:23][C:22]([C@@H:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][CH2:45][C:44]3[CH:43]=[CH:42][C:41]([C:37]4[CH:36]=[N:35][CH:40]=[CH:39][CH:38]=4)=[CH:48][CH:47]=3)[CH:3]=2)[N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:27][CH:26]=1)[CH3:34]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 36930464-(Pyridin-3-yl)benzaldehydeHCID 11590834HCID 11590834, compoundHCID 178419135HCID 178419135, compound

Product 1

HCID 10392326HCID 10392326, compoundYield 113.3%

Procedure

Using the same method as for COMPOUND 17 and using INTERMEDIATE 5a (205 mg, 0.44 mmol), 4-(3-pyridinyl)benzaldehyde (88.7 mg, 0.48 mmol), and decaborane (16.4 mg, 0.13 mmol) afforded COMPOUND 52 (266 mg, 61% yield) as its TFA salt. This material was lyophilized from CH3CN/H2O to produce a slightly yellow solid.

Sources & evidence

ORD record
ord-61407ac0d4724b6e936ac46ea9f803fc
Source dataset
uspto-grants-2007_07
Patent number
US07241764B2

Reaction notes

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