1-Boc-octahydropyrrolo(3,4-b)pyridine → [1-(6,7-Dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-yl)-azetidin-3-yl]-amine

HRID 1027906Notes

Reaction equation

HRID 1027906 reaction equation
[N:1]1([C:10](OC(C)(C)C)=O)[CH2:6][CH2:5][CH2:4][CH:3]2[CH2:7][NH:8][CH2:9][CH:2]12.CC1C=CC(S(OC2C3CCC[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>>[N:31]1[C:30]2[C:34]3[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=3[CH2:7][CH2:3][CH2:4][C:5]=2[C:6]([N:1]2[CH2:2][CH:9]([NH2:8])[CH2:10]2)=[N:33][CH:32]=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 25072258[1-(6,7-Dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-yl)-azetidin-3-yl]-amine

Procedure

The title compound was prepared using the procedure outlined in Example 59D substituting Example 2B 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 2.20-2.36 (m, 4H), 2.36-2.40 (m, 3H), 2.60 (t, 2H), 3.65-3.74 (m, 1H), 4.06 (dd, 2H), 4.47-4.55 (m, 2H), 7.26-7.34 (m, 1H), 7.36-7.43 (m, 2H), 7.62-7.67 (m, 1H), 8.41-8.44 (m, 1H). MS (M+H)+ m/z 281.

Sources & evidence

ORD record
ord-622ece6098d64a359597faafea3fe9af
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

Loading…