1-Boc-octahydropyrrolo(3,4-b)pyridine → 4-(3-(R)-Methylamino-pyrrolidin-1-yl)-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidine

HRID 1027905Notes

Reaction equation

HRID 1027905 reaction equation
[N:1]1([C:10](OC(C)(C)C)=O)CCC[CH:3]2[CH2:7][NH:8][CH2:9][CH:2]12.CC1C=CC(S(O[C:28]2[C:29]3[CH2:38][CH2:37][CH2:36][C:35]4[CH:39]=[CH:40][CH:41]=[CH:42][C:34]=4[C:30]=3[N:31]=[CH:32][N:33]=2)(=O)=O)=CC=1.CC1C=CC(S(OC2C3CCCC4C=CC=CC=4C=3N=C(N)N=2)(=O)=O)=CC=1>>[CH3:10][NH:1][C@@H:2]1[CH2:3][CH2:7][N:8]([C:28]2[C:29]3[CH2:38][CH2:37][CH2:36][C:35]4[CH:39]=[CH:40][CH:41]=[CH:42][C:34]=4[C:30]=3[N:31]=[CH:32][N:33]=2)[CH2:9]1

Participants

4

Reactant 3

HCID 225622021-Boc-octahydropyrrolo(3,4-b)pyridineHCID 251291732-amino-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-yl 4-methylbenzenesulfonateHCID 866219036,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-yl 4-methylbenzenesulfonate

Product 1

HCID 250722594-(3-(R)-Methylamino-pyrrolidin-1-yl)-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidine

Procedure

The title compound was prepared using the procedure outlined in Example 59D substituting Example 1E for t-butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate, and substituting the product from Example 118C for the product from Example 59C, followed by the procedure outlined in Example 59E. 1H NMR (CD3OD) δ 1.84-1.98 (m, 1H), 2.17-2.27 (m, 1H), 2.28-2.36 (m, 2H), 2.41-2.50 (m, 5H), 2.66 (t, 2H), 3.33-3.40 (m, 1H), 3.52-3.61 (m, 1H), 3.72-3.80 (m, 1H), 3.83-3.93 (m, 2H), 7.27-7.33 (m, 1H), 7.37-7.43 (m, 2H), 7.65-7.71 (m, 1H), 8.40-8.44 (m, 1H). MS (M+H)+ m/z 295.

Sources & evidence

ORD record
ord-c72bc3c8a4cd4e8cac1267ce535ec1c3
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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