HCID 69055164, compound → HCID 11500414, compound

HRID 2100616Notes

Reaction equation

[Cl:1][C:2]1C2C(=O)N[C@H]3CN(C(OC(C)(C)C)=O)C[C@@H]3C=2C(CC)=CC=1.[Cl:25][C:26]1[C:35]2[C:34](=[O:36])[NH:33][C@@H:32]3[CH2:37][N:38](C(OC(C)(C)C)=O)[CH2:39][C@H:31]3[C:30]=2[C:29]([CH2:47][CH3:48])=[CH:28][CH:27]=1>>[ClH:1].[Cl:25][C:26]1[C:35]2[C:34](=[O:36])[N:33]([CH3:2])[C@H:32]3[CH2:37][NH:38][CH2:39][C@@H:31]3[C:30]=2[C:29]([CH2:47][CH3:48])=[CH:28][CH:27]=1

Participants

Reactant 2

HCID 69055164HCID 69055164, compound

HCID 69057614HCID 69057614, compound

Product 1

HCID 11500414HCID 11500414, compound

Procedure

Following the procedures described in Example 15, Part A and Example 45, Part I, (3aR,9bS)-tert-butyl 6-chloro-9-ethyl-5-oxo-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate, the first eluting compound from Example 56, Part B, was converted into the title compound of Example 58 as an pale yellow solid. 1H NMR (DMSO-D6): δ 9.84 (broad s, 1H), 9.79 (broad s, 1H), 7.33 (d, 1H, J=8.2 Hz), 7.26 (d, 1H, J=8.2 Hz), 3.98-3.92 (m, 1H), 3.78-3.71 (m, 1H), 3.62-3.48 (m, 2H), 3.35-3.20 (m, 2H), 2.93 (s, 3H), 2.47 (q, 2H, J=7.4 Hz), 1.05 (t, 3H, J=7.5 Hz). LRMS (ESI): 265.1/267.1 (M+H)+.

Sources & evidence

ORD record: ord-cd4b6dd4e6a2473482027d262116244c
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572805B2

Reaction notes

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