HCID 68887553, compound → HCID 68891382, compound

HRID 857895Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:26])[CH2:21][CH2:20]3)=[CH:15][C:16]([C:17]#[N:18])=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O[C:40]([N:42]1CCN2C(C3CCN(C(OCC4C=CC=CC=4)=O)CC3)=C(C#N)C=C2C1)=O)(C)(C)C>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH:19]3[CH2:20][CH2:21][N:22]([C:25]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:26])[CH2:23][CH2:24]3)=[C:15]([C:40]#[N:42])[C:16]([C:17]#[N:18])=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 68887553HCID 68887553, compound

HCID 68888077HCID 68888077, compound

Product 1

HCID 68891382HCID 68891382, compound

Procedure

By proceeding in a similar manner to that described in Reference Example 8 but using a mixture of 6-(1-benzyloxycarbonylpiperidin-4-yl)-8-cyano-3,4-dihydro-1H-pyrrolo[1,2-a]pyrazine-2-carboxylic acid tert-butyl ester and 6-(1-benzyloxycarbonylpiperidin-4-yl)-7-cyano-3,4-dihydro-1H-pyrrolo[1,2-a]pyrazine-2-carboxylic acid tert-butyl ester (5.00 g, Reference Example 15) the title compound (4.71 g) was prepared as a yellow oil, MS: 490 [MH]+. 1H NMR [(CDCl3]: δ 7.42–7.30 (m, 5H), 5.15 (s, 2H), 4.71 (s, 2H), 4.50–4.28 (bs, 2H), 3.92 (t, 2H), 3.86 (t, 2H), 2.93–2.72 (m, 3H), 2.20–1.93 (bs, 2H), 1.80 (d, 2H) and 1.51 (s, 9H).

Sources & evidence

ORD record: ord-3a8008c540c24e88a2320671c593111b
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148215B2

Reaction notes

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