Ethyl isocyanate → HCID 178465490, compound

HRID 715573Notes

Reaction equation

HRID 715573 reaction equation
[Si:1]([O:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@@H:16]([O:17][C:18]3[N:40]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[C:21]4=[N:22][C:23]([C:27]5[CH:32]=[CH:31][C:30]([C@H:33]6[CH2:38][CH2:37][C@H:36]([OH:39])[CH2:35][CH2:34]6)=[CH:29][CH:28]=5)=[C:24]([Cl:26])[CH:25]=[C:20]4[N:19]=3)[C@H:12]2[O:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[N:56]([CH2:59][CH3:60])=[C:57]=[O:58]>O1CCCC1>[CH2:59]([NH:56][C:57](=[O:58])[O:39][C@H:36]1[CH2:37][CH2:38][C@H:33]([C:30]2[CH:31]=[CH:32][C:27]([C:23]3[N:22]=[C:21]4[N:40]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[C:18]([O:17][C@@H:16]5[CH2:15][O:14][C@@H:13]6[C@H:9]([O:8][Si:1]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2])[CH2:10][O:11][C@H:12]56)=[N:19][C:20]4=[CH:25][C:24]=3[Cl:26])=[CH:28][CH:29]=2)[CH2:34][CH2:35]1)[CH3:60]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanate2×HCID 8471Triethylamine2×HCID 178455386HCID 178455386, compound

Product 1

HCID 178465490HCID 178465490, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(trans)-4-(4-(2-((3R,3aR,6R,6aS)-6-(tert-Butyldimethylsilyloxy)hexahydrofuro[3,2-b]-furan-3-yloxy)-6-chloro-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]py-ridin-5-yl)phenyl)cyclohexanol (50 mg) and triethylamine (20 μL) are dissolved in tetrahydrofurane (2 mL), treated with isocyanatoethane (8 μL) and stirred for 12 hours. Triethylamine (20 μL) and isocyanatoethane (8 μL) are added and the mixture is stirred for 48 hours. The mixture is partitioned between ethylacetate and saturated aqueous NH4Cl solution. The organic phase is dried (MgSO4) and concentrated. The residue is purified by HPLC on reversed phase to give the title compound. LC (method 5): tR=1.26 min; Mass spectrum (ESI+): m/z=787 [M+H]+.

Workup

  1. stirringthe mixture is stirred for 48 hours
  2. customThe mixture is partitioned between ethylacetate and saturated aqueous NH4Cl solution
  3. dry with materialThe organic phase is dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is purified by HPLC on reversed phase

Sources & evidence

ORD record
ord-1fa014e98a2e4624b68b6fff04c2b7de
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

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