Tert-Butylamine → N-tert-Butyl-3-[2-methyl-4-(6-pyrrolidin-1-yl-pyrido[3,4-d]pyrimidin-4-ylamino)-phenoxy]-benzamide

HRID 731917Notes

Reaction equation

HRID 731917 reaction equation
[CH3:1][C:2]1[CH:17]=[C:16]([NH:18][C:19]2[C:20]3[CH:28]=[C:27]([N:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)[N:26]=[CH:25][C:21]=3[N:22]=[CH:23][N:24]=2)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](O)=[O:9].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[C:65]([NH2:69])([CH3:68])([CH3:67])[CH3:66]>CN(C=O)C>[C:65]([NH:69][C:8](=[O:9])[C:7]1[CH:11]=[CH:12][CH:13]=[C:5]([O:4][C:3]2[CH:14]=[CH:15][C:16]([NH:18][C:19]3[C:20]4[CH:28]=[C:27]([N:29]5[CH2:33][CH2:32][CH2:31][CH2:30]5)[N:26]=[CH:25][C:21]=4[N:22]=[CH:23][N:24]=3)=[CH:17][C:2]=2[CH3:1])[CH:6]=1)([CH3:68])([CH3:67])[CH3:66]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 690519883-[2-Methyl-4-(6-pyrrolidin-1-yl-pyrido[3,4-d]pyrimidin-4-ylamino)-phenoxy]-benzoic acid

Product 1

HCID 69052036N-tert-Butyl-3-[2-methyl-4-(6-pyrrolidin-1-yl-pyrido[3,4-d]pyrimidin-4-ylamino)-phenoxy]-benzamideYield 35.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-[2-Methyl-4-(6-pyrrolidin-1-yl-pyrido[3,4-d]pyrimidin-4-ylamino)-phenoxy]-benzoic acid (72 mg, 0.16 mmol), HATU (93 mg, 0.24 mmol), NEt3 (50 mg, 0.48 mmol), and tert-butyl amine (24 mg, 0.33 mmol) in DMF (1.5 mL) was shaken at 60° C. for 12 h. The reaction was concentrated and purified by preparative HPLC to give a yellow solid (28 mg, 35%). LRMS: 497.3 (MH+); 1H NMR (DMSO-d6, 400 MHz): δ 9.65 (s, 1H), δ 8.81 (s, 1H), δ 8.36 (s, 1H), δ 7.77-7.81 (m, 3H), δ 7.54 (d, J=7.78, 1H), δ 7.42 (t, J=7.78, 1H), δ 7.34-7.35 (m, 1H), δ 7.14 (s, 1H), δ 7.00-7.069 (m, 2H), δ 3.50-3.54 (m, 4H), δ 2.21 (s, 3H), δ 2.00-2.09 (m, 4H), δ 1.37 (s, 9H).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-b753ed2ad9724f11b971985fdda2afaf
Source dataset
uspto-grants-2009_09
Patent number
US07585869B2

Reaction notes

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