tert-Butyl piperazine-1-carboxylate → 8-Phenyl-4-(piperazin-1-yl)-5,6,7,8-tetrahydroquinazolin-2-amine

HRID 2088716Notes

Reaction equation

HRID 2088716 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][NH:29][CH2:28][CH2:27]1.N1C[CH2:42][C@@H:41](NC(=O)OC(C)(C)C)[CH2:40]1>>[C:19]1([CH:20]2[C:12]3[N:17]=[C:16]([NH2:18])[N:15]=[C:14]([N:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)[C:13]=3[CH2:23][CH2:22][CH2:21]2)[CH:24]=[CH:42][CH:41]=[CH:40][CH:25]=1

Participants

4

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 866348802-amino-9,9-dimethyl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-4-yl 4-methylbenzenesulfonate

Product 1

HCID 444668728-Phenyl-4-(piperazin-1-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 tert-butyl piperazine-1-carboxylate for (R)-tert-butyl pyrrolidin-3-ylcarbamate. 1H NMR (300 MHz, CDCl3) δ 7.24 (m, 2H), 7.18 (m, J=7.54 Hz, 1H), 7.06 (d, J=8.33 Hz, 1H), 4.55 (s, 2H), 3.99 (t, J=6.94 Hz, 1H), 3.31 (m, 4H), 2.98 (m, 4H), 2.55 (m, 2H), 2.20 (m, 1H), 1.79 (m, 3H); MS (ESI+) m/z 310 (M+H)+.

Sources & evidence

ORD record
ord-1105f770ca794605be99613fd3bc974f
Source dataset
uspto-grants-2013_05
Patent number
US08436005B2

Reaction notes

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