5,6,7,8-Tetrahydroimidazo(1,2-a)pyrazine → HCID 90314122, compound

HRID 1422640Notes

Reaction equation

HRID 1422640 reaction equation
C[O:2][C:3](=[O:38])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@H:15]3[C:23]4[C:18](=[C:19]([CH2:28][N:29]5[CH2:34][CH2:33][N:32]6[CH:35]=[CH:36][N:37]=[C:31]6[CH2:30]5)[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1.COC(=O)C[C@H]1C2C=CC(O[C@H]3C4C(=C(CBr)C(C(F)(F)F)=CC=4)CC3)=CC=2OC1.N1C=CN2CCNCC=12>>[N:37]1[CH:36]=[CH:35][N:32]2[CH2:33][CH2:34][N:29]([CH2:28][C:19]3[C:20]([C:24]([F:25])([F:27])[F:26])=[CH:21][CH:22]=[C:23]4[C:18]=3[CH2:17][CH2:16][C@H:15]4[O:14][C:12]3[CH:11]=[CH:10][C:9]4[C@H:5]([CH2:4][C:3]([OH:38])=[O:2])[CH2:6][O:7][C:8]=4[CH:13]=3)[CH2:30][C:31]=12

Participants

4

Reactant 3

HCID 132470465,6,7,8-Tetrahydroimidazo(1,2-a)pyrazineHCID 86700813{(S)-6-[(R)-4-Bromomethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl esterHCID 90314440{(S)-6-[(R)-4-(5,6-dihydro-8H-imidazo[1,2-a]pyrazin-7-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

Product 1

HCID 90314122HCID 90314122, compound

Procedure

The methyl ester of the title compound, {(S)-6-[(R)-4-(5,6-dihydro-8H-imidazo[1,2-a]pyrazin-7-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester, is prepared from {(S)-6-[(R)-4-bromomethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester and 5,6,7,8-tetrahydro-imidazo[1,2-a]pyrazine following a procedure analogous to that described for Intermediate 42. The crude product is directly submitted to the saponification conditions described for Example 1 to give the title compound upon chromatography on reversed phase (HPLC; acetonitrile/water). LC (method 6): tR=0.76 min; Mass spectrum (ESI+): m/z=514 [M+H]+.

Sources & evidence

ORD record
ord-ab4998f89b47400a8c8b424fbe711bca
Source dataset
uspto-grants-2015_01
Patent number
US08927531B2

Reaction notes

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