Morpholine → HCID 67440295, compound

HRID 1471510Notes

Reaction equation

HRID 1471510 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:7]([C:9]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:30]=[CH:29][C:24]3[B:25]([OH:28])[O:26][CH2:27][C:23]=3[CH:22]=2)=[CH:16][C:10]=1[O:11][CH2:12][C:13](O)=[O:14])#[N:8]>>[OH:28][B:25]1[C:24]2[CH:29]=[CH:30][C:21]([O:20][C:17]3[CH:18]=[CH:19][C:9]([C:7]#[N:8])=[C:10]([O:11][CH2:12][C:13]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[O:14])[CH:16]=3)=[CH:22][C:23]=2[CH2:27][O:26]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 67440422HCID 67440422, compound

Product 1

HCID 67440295HCID 67440295, compound

Procedure

Following the general procedure, morpholine (80 μL, 0.93 mmol) was coupled with [2-cyano-5-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-5-yloxy)-phenoxy]-acetic acid ((D39), 150 mg, 0.46 mmol) to give a crude oil containing (D41). Purification by reverse phase HPLC followed by lyophilization gave a white solid of (D41) (38 mg, 21%). 1H NMR 400 MHz (d6-DMSO) δ: 9.32 (br s, 1H), 7.86 (d, J=8.5 Hz, 1H), 7.78 (d, J=8.5 Hz, 1H), 7.21 (br s, 1H), 7.15 (dd, J=9.0, 1.5 Hz, 1H), 6.90 (d, J=1.5 Hz, 1H), 6.65 (dd, J=8.5, 1.5 Hz, 1H), 5.17 (s, 2H), 5.03 (s, 2H), 3.65-3.55 (m, 4H), 3.49-3.40 (m, 4H); MS (ES) m/z: 395 (M+H)+; HPLC purity 96.02% (Maxplot), 97.64% (220 nm) and 97.18% (254 nm).

Workup

  1. customto give a crude oil
  2. additioncontaining (D41)
  3. customPurification by reverse phase HPLC
  4. customgave a white solid of (D41) (38 mg, 21%)

Sources & evidence

ORD record
ord-b833268b936d4914905c1743db5dcd52
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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