Ethyl isocyanate → HCID 178458019, compound

HRID 715580Notes

Reaction equation

HRID 715580 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]([CH:59]([CH3:61])[CH3:60])=[C:57]=[O:58].N(CC)=C=O>CN(C)C1C=CN=CC=1.O1CCCC1>[CH: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)([CH3:61])[CH3:60]

Participants

7

Reactant 4

HCID 8022Ethyl isocyanate2×HCID 8471Triethylamine3×HCID 61277Isopropyl isocyanateHCID 178455385HCID 178455385, compound

Product 1

HCID 178458019HCID 178458019, 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 2-isocyanatopropane (14 μL) and stirred for 12 hours. Triethylamine (60 μL) and isocyanatoethane (28 μL) are added and the mixture is stirred for 12 hours at 70° C. Again triethylamine (60 μL) and isocyanatoethane (28 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.

Workup

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

Sources & evidence

ORD record
ord-2086606c087949d9bc9200c60bd6d458
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

Loading…