4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrazine → HCID 90314831, compound

HRID 1422642Notes

Reaction equation

HRID 1422642 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[NH:35][CH:36]=[CH:37][C:31]6=[CH: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.N1N2CCNCC2=CC=1>>[NH:35]1[N:32]2[CH2:33][CH2:34][N:29]([CH2:28][C:19]3[C:20]([C:24]([F:27])([F:25])[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)[CH:30]=[C:31]2[CH:37]=[CH:36]1

Participants

4

Reactant 3

HCID 219414014,5,6,7-Tetrahydropyrazolo[1,5-a]pyrazineHCID 86700813{(S)-6-[(R)-4-Bromomethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl esterHCID 90314077HCID 90314077, compound

Product 1

HCID 90314831HCID 90314831, compound

Procedure

The methyl ester of the title compound, {(S)-6-[(R)-4-(6,7-dihydro-pyrazolo[1,5-a]pyrazin-5-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 4,5,6,7-tetrahydro-pyrazolo[1,5-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=1.07 min; Mass spectrum (ESI+): m/z=514 [M+H]+.

Sources & evidence

ORD record
ord-f821d654bc06426f8499a63f9254b54b
Source dataset
uspto-grants-2015_01
Patent number
US08927531B2

Reaction notes

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