(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine → 8-phenyl-4-((4aR,7aR)-tetrahydro-1H-pyrrolo[3,4-b]pyridin-6(2H,7H,7aH)-yl)-5,6,7,8-tetrahydroquinazolin-2-amine

HRID 2088717Notes

Reaction equation

HRID 2088717 reaction equation
CC1C=CC(S(O[C:12]2[C:13]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]([CH3:25])([CH3:24])[C:14]=3[N:15]=[C:16]([NH2:18])[N:17]=2)(=O)=O)=CC=1.[N:26]1(C(OC(C)(C)C)=O)[CH2:31][CH2:30][CH2:29][C@@H:28]2[CH2:32][NH:33][CH2:34][C@H:27]12.N1C[CH2:45][C@@H:44](NC(=O)OC(C)(C)C)[CH2:43]1>>[C:19]1([CH:20]2[C:12]3[N:17]=[C:16]([NH2:18])[N:15]=[C:14]([N:33]4[CH2:32][C@@H:28]5[C@@H:27]([NH:26][CH2:31][CH2:30][CH2:29]5)[CH2:34]4)[C:13]=3[CH2:23][CH2:22][CH2:21]2)[CH:24]=[CH:45][CH:44]=[CH:43][CH:25]=1

Participants

4

Reactant 3

HCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 1519436rel-1,1-Dimethylethyl (4aR,7aR)-octahydro-1H-pyrrolo(3,4-b)pyridine-1-carboxylateHCID 866348802-amino-9,9-dimethyl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-4-yl 4-methylbenzenesulfonate

Product 1

HCID 444629548-phenyl-4-((4aR,7aR)-tetrahydro-1H-pyrrolo[3,4-b]pyridin-6(2H,7H,7aH)-yl)-5,6,7,8-tetrahydroquinazolin-2-amine

Procedure

The title compound was prepared according to the procedures of Examples 1E and 1F, substituting the product from Example 9C for the product from Example 1D and substituting (4aR,7aR)-tert-butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate for (R)-tert-butyl pyrrolidin-3-ylcarbamate. 1H NMR (300 MHz, CDCl3) δ 7.22 (m, J=4.36 Hz, 2H), 7.16 (m, 1H), 7.09 (d, J=8.33 Hz, 1H), 7.02 (d, J=8.72 Hz, 1H), 4.40 (s, 2H), 3.89 (m, 3H), 3.52 (m, 3H), 3.03 (m, 1H), 2.72 (m, 3H), 2.26 (m, 3H), 1.74 (m, 6H); MS (ESI+) m/z 350 (M+H)+.

Sources & evidence

ORD record
ord-e88e9d94d930429eb9da17dac65f7911
Source dataset
uspto-grants-2013_05
Patent number
US08436005B2

Reaction notes

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