1-Boc-octahydropyrrolo(3,4-b)pyridine → 4'-((4aR,7aR)-tetrahydro-1H-pyrrolo[3,4-b]pyridin-6(2H,7H,7aH)-yl)-6',7'-dihydro-5'H-spiro[cyclopentane-1,8'-quinazolin]-2'-amine

HRID 2059752Notes

Reaction equation

HRID 2059752 reaction equation
[N:1]1(C(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(O[C:28]2[C:37]3[CH2:36][CH2:35][CH2:34][C:33]4([CH2:41][CH2:40][CH2:39][CH2:38]4)[C:32]=3[N:31]=[C:30]([NH2:42])[N:29]=2)(=O)=O)=CC=1>>[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]2[CH2:7][N:8]([C:28]3[C:37]4[CH2:36][CH2:35][CH2:34][C:33]5([CH2:41][CH2:40][CH2:39][CH2:38]5)[C:32]=4[N:31]=[C:30]([NH2:42])[N:29]=3)[CH2:9][C@H:2]12

Participants

3

Reactant 2

HCID 225622021-Boc-octahydropyrrolo(3,4-b)pyridineHCID 866343332'-amino-6',7'-dihydro-5'H-spiro[cyclopentane-1,8'-quinazolin]-4'-yl 4-methylbenzenesulfonate

Product 1

HCID 468818894'-((4aR,7aR)-tetrahydro-1H-pyrrolo[3,4-b]pyridin-6(2H,7H,7aH)-yl)-6',7'-dihydro-5'H-spiro[cyclopentane-1,8'-quinazolin]-2'-amine

Procedure

The title compound was prepared using the procedures outlined in Examples 1G and 1H, substituting tert-butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate (CAS# 159877-36-8) for the product from Example 1D. 1H NMR (300 MHz, CDCl3) δ 4.38-4.47 (m, 2 H), 3.70-3.82 (m, 2 H), 3.38-3.52 (m, 2 H), 3.31 (td, 1 H), 3.00 (dt, 1 H), 2.57-2.69 (m, 3 H), 2.16-2.26 (m, 2 H), 1.96-2.07 (m, 1 H), 1.79-1.92 (m, 2 H), 1.64-1.76 (m, 6 H), 1.42-1.59 (m, 6 H). MS (DCI+) m/z 328 (M+H).

Sources & evidence

ORD record
ord-1c0d7d5413334972a931356f0ea0c19b
Source dataset
uspto-grants-2012_10
Patent number
US08278313B2

Reaction notes

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