Diisopropylethylamine → HCID 59232045, compound

HRID 1099299Notes

Reaction equation

[NH2:1][C:2]1[C:7]2=[C:8]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]4[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=4[F:35])=[O:23])=[C:17]([F:36])[CH:16]=3)[CH:9]=[C:10]([C:11](=[O:14])[CH2:12]Br)[N:6]2[N:5]=[CH:4][N:3]=1.C(N(C(C)C)CC)(C)C.[N:46]1([CH2:52][CH2:53][CH2:54][OH:55])[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1>CS(C)=O>[NH2:1][C:2]1[C:7]2=[C:8]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]4[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=4[F:35])=[O:23])=[C:17]([F:36])[CH:16]=3)[CH:9]=[C:10]([C:11](=[O:14])[CH2:12][O:55][CH2:54][CH2:53][CH2:52][N:46]3[CH2:51][CH2:50][O:49][CH2:48][CH2:47]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a stirred solution of Example 257 (200 mg, 0.351 mmol) in DMSO (1 mL), was added diisopropylethylamine (435 μL, 2.64 mmol) and 3-morpholin-4-ylpropan-1-ol (364 μL, 2.64 mmol) at rt. The reaction was allowed to stir at 40° C. for 17 hr. The mixture was allowed to cool and purified by preparative HPLC using a gradient elution from 10% to 70% acetonitrile to obtain 37 mg (17%) of the desired product. 1H-NMR (DMSO-d6) δ 9.62 (br s, 1H), 9.47 (br s, 1H), 8.65 (dd, J=2.4, 7.2 Hz, 1H), 8.23 (t, J=8.4 Hz, 1H), 7.92 (s, 1H), 7.54-7.47 (m, 1H), 7.42-7.38 (m, 1H), 7.31 (dd, J=2.1, 12.3 Hz, 1H), 7.22 (d, J=8.1 Hz, 1H), 6.88 (s, 1H), 4.24 (d, J=11.7 Hz, 2H), 4.05-3.96 (m, 4H), 3.86-3.77 (m, 4H), 3.43 (t, J=5.7 Hz, 2H), 3.24-3.20 (m, 2H), 1.91-1.85 (m, 2H); MS [M+H]+=634.2; LCMS RT=2.75 min.

Workup

temperatureto cool
custompurified by preparative HPLC
washa gradient elution from 10% to 70% acetonitrile

Sources & evidence

ORD record: ord-b99d1a86f8a34c0da1e9b0c111f62531
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143393B2

Reaction notes

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