Ethyl isocyanate → HCID 178465489, compound

HRID 715579Notes

Reaction equation

HRID 715579 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]>CN(C)C1C=CN=CC=1.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

6

Reactant 3

HCID 8022Ethyl isocyanate2×HCID 8471Triethylamine2×HCID 178455385HCID 178455385, compound

Product 1

HCID 178465489HCID 178465489, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(cis)-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]pyridin-5-yl)phenyl)cyclohexanol (50 mg), 4-dimethylamino-pyridine (DMAP, 1 mg) and triethylamine (30 μL) are dissolved in tetrahydrofurane (1 mL), treated with isocyanatoethane (11 μL) and stirred for 6 hours. Triethylamine (60 μL) and isocyanatoethane (22 μL) are added and the mixture is stirred for 12 hours at 70° C. The mixture is partitioned between ethylacetate and saturated aqueous NH4Cl solution. The organic phase is dried (MgSO4) and concentrated. The residue is used directly in the next step. LC (method 4): tR=1.20 min; Mass spectrum (ESI+): m/z=787 [M+H]+.

Workup

  1. stirringthe mixture is stirred for 12 hours at 70° C
  2. customThe mixture is partitioned between ethylacetate and saturated aqueous NH4Cl solution
  3. dry with materialThe organic phase is dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-92fe7a4ab02c472581c48eea24cc7704
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

Loading…