Aniline → HCID 11371281, compound

HRID 239873Notes

Reaction equation

HRID 239873 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18](O)=[O:19])=[CH:13][CH:12]=2)[NH:4][N:3]=1.C(N(C(C)C)CC)(C)C.CN(C(O[N:38]1N=N[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.NC1C=CC=CC=1>C1COCC1>[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]2[CH:12]=[CH:13][C:14]([CH2:17][C:18]([NH:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:19])=[CH:15][CH:16]=2)[NH:4][N:3]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66680818HCID 66680818, compound

Product 1

HCID 11371281HCID 11371281, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 53B (40 mg, 015 mmol), diisopropylethylamine (0.078 mL, 0.45 mmol), TBTU (57 mg, 0.18 mmol), and aniline in THF (1 mL) was stirred for 18 hours at room temperature and concentrated. The residue was purified by preparative HPLC using the conditions described in Example 15H to provide 15 mg of the desired product as the trifluoroacetate salt. MS (ESI(+)) m/e 343 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 3.74 (s, 2H), 6.84 (dd, J=5.09, 3.05 Hz, 1H), 7.02-7.07 (m, 1H), 7.28-7.33 (m, 4H), 7.43-7.50 (m, 4H), 7.62 (d, J=7.80 Hz, 2H).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-a7f9b17c9740419887afc79268786da1
Source dataset
uspto-grants-2014_02
Patent number
US08642776B2

Reaction notes

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