tert-Butanol → HCID 178452647, compound

HRID 16682Notes

Reaction equation

HRID 16682 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:19][C:18]3[C:13](=[N:14][C:15](C(O)=O)=[CH:16][CH:17]=3)[C:12]=2[NH:23][C:24]([C@H:26]2[CH2:31][CH2:30][C@H:29]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][C:33]3=[O:38])[CH2:28][CH2:27]2)=[O:25])=[O:10])=[N:6][CH:7]=1.C([N:41]([CH2:44]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:53])C=CC=CC=1.[C:63]([OH:67])([CH3:66])([CH3:65])[CH3:64]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:19][C:18]3[C:13](=[N:14][C:15]([NH:41][C:44](=[O:53])[O:67][C:63]([CH3:66])([CH3:65])[CH3:64])=[CH:16][CH:17]=3)[C:12]=2[NH:23][C:24]([C@H:26]2[CH2:27][CH2:28][C@H:29]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][C:33]3=[O:38])[CH2:30][CH2:31]2)=[O:25])=[O:10])=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 178524191HCID 178524191, compound

Product 1

HCID 178452647HCID 178452647, compound

Conditions

Temperature
100 °C

Procedure

2-{[(5-Chloropyridin-2-yl)amino]carbonyl}-3-({[trans-4-(3-oxomorpholin-4-yl)cyclohexyl]carbonyl}amino)furo[3,2-b]pyridine-5-carboxylic acid (6.80 g) obtained in Example 79 is suspended in t-butanol (300 ml). To the suspension are added triethylamine (3.48 ml) and diphenylphosphoryl azide (5.39 ml) at room temperature, and the mixture is stirred at 100° C. for 15 hours. The reaction solution is concentrated under reduced pressure. The residue is diluted with chloroform, and washed with water and saturated brine. The organic layer is dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: chloroform/methanol=100/1 followed by 20/1) to give the title compound (5.64 g).

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. additionThe residue is diluted with chloroform
  3. washwashed with water and saturated brine
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (eluent: chloroform/methanol=100/1 followed by 20/1)

Sources & evidence

ORD record
ord-eacb4e0701ab439ab75c4823cf750437
Source dataset
uspto-grants-2010_06
Patent number
US07737161B2

Reaction notes

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