Trifluoroacetic acid → (E)-4-(8-Morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)benzoic acid trifluoroacetic acid salt

HRID 1772701Notes

Reaction equation

HRID 1772701 reaction equation
Br[C:2]1[N:7]2[CH:8]=[C:9](/[CH:11]=[CH:12]/[C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[N:10]=[C:6]2[C:5]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:4][CH:3]=1.C([O:33][C:34]([C:36]1[CH:41]=[CH:40][C:39](B2OC(C)(C)C(C)(C)O2)=[CH:38][CH:37]=1)=[O:35])(C)(C)C.[C:51]([OH:57])([C:53]([F:56])([F:55])[F:54])=[O:52]>>[F:54][C:53]([F:56])([F:55])[C:51]([OH:57])=[O:52].[O:26]1[CH2:27][CH2:28][N:23]([C:5]2[C:6]3[N:7]([CH:8]=[C:9](/[CH:11]=[CH:12]/[C:13]4[CH:22]=[CH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[N:14]=4)[N:10]=3)[C:2]([C:39]3[CH:40]=[CH:41][C:36]([C:34]([OH:35])=[O:33])=[CH:37][CH:38]=3)=[CH:3][N:4]=2)[CH2:24][CH2:25]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 43767661,1-Dimethylethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateHCID 117728505(E)-4-(5-Bromo-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-8-yl)morpholine

Product 1

HCID 117728004(E)-4-(8-Morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)benzoic acid trifluoroacetic acid salt

Procedure

The title compound was prepared from compound 2b and 4-(tert-butoxycarbonyl)phenylboronic acid pinacol ester using the methods described in Example 1, Step G, followed by the deprotection of the resulting product with TFA using the methods described in Example 6, Step B. Mass Spectrum (LCMS, ESI pos.) Calcd. for C28H23N5O3: 478.2 [M+H]. found 478.1.

Sources & evidence

ORD record
ord-427ad22895d04c22b48460bfdb3fb69c
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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