4-Morpholinecarbonyl chloride → HCID 178455390, compound

HRID 715572Notes

Reaction equation

HRID 715572 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].[N:49]1([C:55](Cl)=[O:56])[CH2:54][CH2:53][O:52][CH2:51][CH2:50]1>N1C=CC=CC=1>[N:49]1([C:55]([O:39][C@H:36]2[CH2:37][CH2:38][C@H:33]([C:30]3[CH:31]=[CH:32][C:27]([C:23]4[N:22]=[C:21]5[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]6[CH2:15][O:14][C@@H:13]7[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]67)=[N:19][C:20]5=[CH:25][C:24]=4[Cl:26])=[CH:28][CH:29]=3)[CH2:34][CH2:35]2)=[O:56])[CH2:54][CH2:53][O:52][CH2:51][CH2:50]1

Participants

4

Reactant 2

HCID 848104-Morpholinecarbonyl chloride3×HCID 178455386HCID 178455386, compound

Product 1

HCID 178455390HCID 178455390, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

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]pyridin-5-yl)phenyl)cyclohexanol (50 mg) is dissolved in pyridine (1 mL), treated with morpholine-4-carbonyl chloride (25 μL) and stirred for 12 hours at 50° C. Morpholine-4-carbonyl chloride (25 μL) is added and the mixture is stirred for 2 hours at 50° C. Then morpholine-4-carbonyl chloride (75 μL) is added and the mixture is stirred for 48 hours at 70° C. The mixture is partitioned between ethylacetate and hydrochloric acid (1 M). The organic phase is dried (MgSO4) and concentrated. The crude product is used directly in the next step.

Workup

  1. stirringthe mixture is stirred for 2 hours at 50° C
  2. stirringthe mixture is stirred for 48 hours at 70° C
  3. customThe mixture is partitioned between ethylacetate and hydrochloric acid (1 M)
  4. dry with materialThe organic phase is dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-002a6db81f7447c0a5172c3459257beb
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

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