tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate → HCID 68677244, compound

HRID 1989051Notes

Reaction equation

HRID 1989051 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[CH2:21]([O:23][C:24]([C:26]1[C:27](=[O:49])[C:28]2[CH:33]=[N:32][C:31](S(C)(=O)=O)=[N:30][C:29]=2[N:38]([C:40]2[CH:41]=[C:42]3[C:46](=[CH:47][CH:48]=2)[CH2:45][CH2:44][CH2:43]3)[CH:39]=1)=[O:25])[CH3:22]>>[CH2:21]([O:23][C:24]([C:26]1[C:27](=[O:49])[C:28]2[CH:33]=[N:32][C:31]([NH:20][C:17]3[CH:16]=[CH:15][C:14]([CH:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)=[CH:19][CH:18]=3)=[N:30][C:29]=2[N:38]([C:40]2[CH:41]=[C:42]3[C:46](=[CH:47][CH:48]=2)[CH2:45][CH2:44][CH2:43]3)[CH:39]=1)=[O:25])[CH3:22]

Participants

3

Reactant 2

HCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylateHCID 252229828-Indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

Product 1

HCID 68677244HCID 68677244, compound

Procedure

Using the procedure outlined in Example 1(g) the title compound was prepared from 4-(4-amino-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (from the previous step, 66 mg, 0.24 mmol) and 8-indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (from Example 1(e), 100 mg, 0.24 mmol). A yellow solid was obtained (75 mg, 51%) after a preparative HPLC (32 mL/min 5-100% MeCN/H2O gradient over 10 min) purification. The Boc group was removed by treatment with TFA in CH2Cl2 (1:1 v/v) to give the title compound. 1H NMR (400 MHz, CDCl3) δ (ppm): 9.31 (s, 1H), 8.54 (s, 1H), 7.42 (d, J=7.9 Hz, 1H), 7.29 (br, 2H), 7.27 (s, 1H), 7.18 (d, J=7.9 Hz, 1H), 6.91 (br, 2H), 4.35 (q, J=7.1 Hz, 2H), 3.52 (m, 2H), 3.16 (br, 2H), 2.97 (m, 4H), 2.68 (m, 1H), 2.22 (m, 2H), 1.95 (m, 2H), 1.35 (t, J=7.1 Hz, 3H).

Workup

  1. customA yellow solid was obtained (75 mg, 51%)
  2. customafter a preparative HPLC (32 mL/min 5-100% MeCN/H2O gradient over 10 min) purification
  3. customThe Boc group was removed by treatment with TFA in CH2Cl2 (1:1 v/v)

Sources & evidence

ORD record
ord-fe759564b85344c38b85f07d2b7029c6
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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