(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine → 4-((R)-3-(methylamino)pyrrolidin-1-yl)-8-phenyl-5,6,7,8-tetrahydroquinazolin-2-amine

HRID 2088718Notes

Reaction equation

HRID 2088718 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.C(O[C:31](=O)[N:32](C)[C@@H:33]1[CH2:37][CH2:36][NH:35][CH2:34]1)(C)(C)C.N1C[CH2:43][C@@H:42](NC(=O)OC(C)(C)C)[CH2:41]1>>[CH3:31][NH:32][C@@H:33]1[CH2:37][CH2:36][N:35]([C:14]2[C:13]3[CH2:23][CH2:22][CH2:21][CH:20]([C:19]4[CH:24]=[CH:43][CH:42]=[CH:41][CH:25]=4)[C:12]=3[N:17]=[C:16]([NH2:18])[N:15]=2)[CH2:34]1

Participants

4

Reactant 3

HCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 7019173tert-Butyl methyl((3R)-pyrrolidin-3-yl)carbamateHCID 866348802-amino-9,9-dimethyl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-4-yl 4-methylbenzenesulfonate

Product 1

HCID 444668714-((R)-3-(methylamino)pyrrolidin-1-yl)-8-phenyl-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 (R)-tert-butylmethyl(pyrrolidin-3-yl)carbamate for (R)-tert-butyl pyrrolidin-3-ylcarbamate. 1H NMR (300 MHz, CDCl3) δ 7.24 (m, 2H), 7.16 (t, J=7.29 Hz, 1H), 7.07 (d, J=7.12 Hz, 2H), 4.53 (s, 2H), 3.96 (t, J=6.27 Hz, 1H), 3.74 (m, 3H), 3.47 (m, 1H), 3.29 (m, 1H), 2.73 (m, 2H), 2.49 (d, J=2.71 Hz, 3H), 2.14 (m, 2H), 1.80 (m, 4H). MS (ESI+) m/z 324 (M+H)+.

Sources & evidence

ORD record
ord-85f223f3252c4322bf9f680e6a13903c
Source dataset
uspto-grants-2013_05
Patent number
US08436005B2

Reaction notes

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